Stadtler Spectral Handbooks (IR, NMR)

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From Bio-Rad Laboratories, Informatics Division About Bio-Rad About Bio-Rad Informatics Division About the Editors History Timeline PDF: From Sadtler to Informatics Division

Handbooks ● ● ● ●

The Sadtler Handbook of Infrared Spectra The Sadtler Handbook of Proton NMR Spectra The Sadtler Handbook of Carbon NMR Spectra The Sadtler Handbook of Mass Spectra (Coming Soon)

Sa dt le r Spe ct r a l H a n dbook s N ow On Sa le

W h ile su pplie s la st , Bio- Ra d is offe r in g t h e w e ll- r e spe ct e d Sa dt le r Spe ct r a l H a n dbook s a t a n ou t st a n din g pr ice .

N ow On ly $ 4 9 Th e se book s con t a in a com pr e h e n sive colle ct ion of h igh qu a lit y I R, N M R, or UV da t a .

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Table of Contents - IR I. II. III. IV. V. VI. VII. VIII.

Hydrocarbons Halogenated Hydrocarbons Nitrogen Containing Compounds Silicon Containing Compounds (Except Si-O) Phosphorus Containing Compounds (Except P-O And P(=O)-O) Sulfur Containing Compounds Oxygen Containing Compounds (Except -C(=O)-) Compounds Containing Carbon To Oxygen Double Bonds

I. Hydrocarbons A. Saturated Hydrocarbons 1. Normal Alkanes 2. Branched Alkanes 3. Cyclic Alkanes B. Unsaturated Hydrocarbons 1. Acyclic Alkenes 2. Cyclic Alkenes 3. Alkynes C. Aromatic Hydrocarbons 1. Monocyclic (Benzenes) 2. Polycyclic II. Halogenated Hydrocarbons A. Fluorinated Hydrocarbons 1. Aliphatic 2. Aromatic B. Chlorinated Hydrocarbons 1. Aliphatic 2. Olefinic 3. Aromatic C. Brominated Hydrocarbons 1. Aliphatic 2. Olefinic 3. Aromatic D. Iodinated Hydrocarbons 1. Aliphatic and Olefinic 2. Aromatic III. Nitrogen Containing Compounds A. Amines 1. Primary a. Aliphatic and Olefinic b. Aromatic 2. Secondary a. Aliphatic and Olefinic

b. Aromatic 3. Tertiary a. Aliphatic and Olefinic b. Aromatic B. Pyridines C. Quinolines D. Miscellaneous Nitrogen Heteroaromatics E. Hydrazines F. Amine Salts G. Oximes (-CH=N-OH) H. Hydrazones (-CH=N-NH2) I. Azines (-CH=N-N=CH-) J. Amidines (-N=CH-N) K. Hydroxamic Acids L. Azo Compounds (-N=N-) M. Triazenes (-N=N-NH-) N. Isocyanates (-N=C=O) O. Carbodiimides (-N=C=N-) P. Isothiocyanates (-N=C=S) Q. Nitriles (-C≡N) 1. Aliphatic 2. Olefinic 3. Aromatic R. Cyanamides (=N-C≡N) S. Thiocyanates (-S-C≡N) T. Nitroso Compounds (-N=O) U. N-Nitroso Compounds (=N-N=O) V. Nitrites (-O-N=O) W. Nitro Compounds (-NO2) 1. Aliphatic 2. Aromatic X. N-Nitro-Compounds (=N-NO2) IV. Silicon Containing Compounds (Except Si-O) V. Phosphorus Containing Compounds (Except P-O and P(=O)-O) VI. Sulfur Containing Compounds A. Sulfides (R-S-R) 1. Aliphatic 2. Heterocyclic 3. Aromatic B. Disulfides (R-S-S-R) C. Thiols 1. Aliphatic 2. Aromatic D. Sulfoxides (R-S(=O)-R) E. Sulfones (R-SO2-R) F. Sulfonyl Halides (R-SO2-X) G. Sulfonic Acids (R-SO2-OH) 1. Sulfonic Acid Salts (R-SO2-O-M) 2. Sulfonic Acid Esters (R-SO2-O-R) 3. Sulfuric Acid Esters (R-O-S(=O)-O-R) H. Thioamides (R-C(=S)-NH2) I. Thioureas (R-NH-C(=S)-NH2)

J. Sulfonamides (R-SO2-NH2) K. Sulfamides (R-NH-SO2-NH-R) VII. Oxygen Containing Compounds (Except -C(=O)-) A. Ethers 1. Aliphatic Ethers (R-O-R) 2. Acetals (R-CH-(-O-R)2) 3. Alicyclic Ethers 4. Aromatic Ethers 5. Furans 6. Silicon Ethers (R3-Si-O-R) 7. Phosphorus Ethers ((R-O)3-P) 8. Peroxides (R-O-O-R) B. Alcohols (R-OH) 1. Primary a. Aliphatic and Alicyclic b. Olefinic c. Aromatic d. Heterocyclic 2. Secondary a. Aliphatic and Alicyclic b. Olefinic c. Aromatic 3. Tertiary a. Aliphatic b. Olefinic c. Aromatic 4. Diols 5. Carbohydrates 6. Phenols VIII. Compounds Containing Carbon To Oxygen Double Bonds A. Ketones (R-C(=O)-R) 1. Aliphatic and Alicyclic 2. Olefinic 3. Aromatic 4. α-Diketones and β-Diketones B. Aldehydes (R-C(=O)-H) C. Acid Halides (R-C(=O)-X) D. Anhydrides (R-C(=O)-O-C(=O)-R) E. Amides 1. Primary (R-C(=O)-NH2) 2. Secondary (R-C(=O)-NH-R) 3. Tertiary (R-C(=O)-N-R2) F. Imides (R-C(=O)-NH-C(=O)-R) G. Hydrazides (R-C(=O)-NH-NH2) H. Ureas (R-NH-C(=O)-NH2) I. Hydantoins, Uracils, Barbiturates J. Carboxylic Acids (R-C(=O)-OH) 1. Aliphatic and Alicyclic 2. Olefinic 3. Aromatic 4. Amino Acids 5. Salts of Carboxylic Acids

K. Esters 1. 2. 3. 4. 5. 6. 7. 8. 9. 10.

Aliphatic Esters of Aliphatic Acids Olefinic Esters of Aliphatic Acids Aliphatic Esters of Olefinic Acids Aromatic Esters of Aliphatic Acids Esters of Aromatic Acids Cyclic Esters (Lactones) Chloroformates Esters of Thio-Acids Carbamates Esters of Phosphorus Acids

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

From Bio-Rad Laboratories, Informatics Division About Bio-Rad About Bio-Rad Informatics Division About the Editors History Timeline PDF: From Sadtler to Informatics Division

Handbooks ● ● ● ●

The Sadtler Handbook of Infrared Spectra The Sadtler Handbook of Proton NMR Spectra The Sadtler Handbook of Carbon NMR Spectra The Sadtler Handbook of Mass Spectra (Coming Soon)

Sa dt le r Spe ct r a l H a n dbook s N ow On Sa le

W h ile su pplie s la st , Bio- Ra d is offe r in g t h e w e ll- r e spe ct e d Sa dt le r Spe ct r a l H a n dbook s a t a n ou t st a n din g pr ice .

N ow On ly $ 4 9 Th e se book s con t a in a com pr e h e n sive colle ct ion of h igh qu a lit y I R, N M R, or UV da t a .

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Table of Contents - Proton NMR I. II. III. IV. V. VI. VII. VIII.

Hydrocarbons Halogenated Hydrocarbons Nitrogen Containing Compounds Silicon Containing Compounds (Except Si-O) Phosphorus Containing Compounds (Except P-O and P(=O)-O) Sulfur Containing Compounds Oxygen Containing Compounds (Except -C(=O)-) Compounds Containing Carbon To Oxygen Double Bonds

I. Hydrocarbons A. Saturated Hydrocarbons 1. Normal Alkanes 2. Branched Alkanes 3. Cyclic Alkanes B. Unsaturated Hydrocarbons 1. Acyclic Alkenes 2. Cyclic Alkenes 3. Alkynes C. Aromatic Hydrocarbons 1. Monocyclic (Benzenes) 2. Polycyclic II. Halogenated Hydrocarbons A. Fluorinated Hydrocarbons 1. Aliphatic 2. Aromatic B. Chlorinated Hydrocarbons 1. Aliphatic 2. Aromatic C. Brominated Hydrocarbons 1. Aliphatic 2. Aromatic D. Iodinated Hydrocarbons 1. Aliphatic 2. Aromatic III. Nitrogen Containing Compounds A. Amines 1. Primary a. Aliphatic b. Aromatic 2. Secondary a. Aliphatic b. Aromatic 3. Tertiary

a. Aliphatic b. Aromatic B. C. D. E. F. G. H. I. J. K. L. M. N. O. P.

Pyridines Quaternary Ammonium Salts Hydrazines Amine Salts Ylidene Compounds (-CH=N-) Oximes (-CH=N-OH) Hydrazones (-CH=N-NH2) Azines (-CH=N-N=CH-) Amidines (-N=CH-N) Hydroxamic Acids Azo Compounds (-N=N-) Isocyanates (-N=C=O) Carbodiimides (-N=C=N-) Isothiocyanates (-N=C=S) Nitriles (-C≡N) 1. Aliphatic 2. Olefinic 3. Aromatic Q. Cyanamides (=N-C≡N) R. Isocyanides (-N≡C ) S. Thiocyanates (-S-C≡N) T. Nitroso Compounds (-N=O) U. N-Nitroso Compounds (=N-N=O) V. Nitrates (-O-NO2) W. Nitrites (-O-N=O) X. Nitro Compounds (-NO2) 1. Aliphatic 2. Aromatic Y. N-Nitro-Compounds (=N-NO2) IV. Silicon Containing Compounds (Except Si-O) V. Phosphorus Containing Compounds (Except P-O and P(=O)-O) VI. Sulfur Containing Compounds A. Sulfides (R-S-R) 1. Aliphatic 2. Aromatic B. Disulfides (R-S-S-R) C. Thiols 1. Aliphatic 2. Aromatic D. Sulfoxides (R-S(=O)-R) E. Sulfones (R-SO2-R) F. Sulfonyl Halides (R-SO2-X) G. Sulfonic Acids (R-SO2-OH) 1. Sulfonic Acid Salts (R-SO2-O-M) 2. Sulfonic Acid Esters (R-SO2-O-R) 3. Sulfuric Acid Esters (R-O-S(=O)-O-R) 4. Sulfuric Acid Salts (R-O-SO2-O-M) H. Thioamides (R-C(=S)-NH2) I. Thioureas (R-NH-C(=S)-NH2)

J. Sulfonamides (R-SO2-NH2) VII. Oxygen Containing Compounds (Except -C(=O)-) A. Ethers 1. Aliphatic Ethers (R-O-R) 2. Alicyclic Ethers 3. Aromatic Ethers 4. Furans 5. Silicon Ethers (R3-Si-O-R) 6. Phosphorus Ethers ((R-O)3-P) B. Alcohols (R-OH) 1. Primary a. Aliphatic b. Olefinic c. Aromatic 2. Secondary a. Aliphatic b. Aromatic 3. Tertiary a. Aliphatic b. Aromatic 4. Diols and Polyols 5. Carbohydrates 6. Phenols VIII. Compounds Containing Carbon To Oxygen Double Bonds A. Ketones (R-C(=O)-R) 1. Aliphatic and Alicyclic 2. Olefinic 3. Aromatic 4. a-Diketones and b-Diketones B. Aldehydes (R-C(=O)-H) C. Acid Halides (R-C(=O)-X) D. Anhydrides (R-C(=O)-O-C(=O)-R) E. Amides 1. Primary (R-C(=O)-NH2) 2. Secondary (R-C(=O)-NH-R) 3. Tertiary (R-C(=O)-N-R2) F. Imides (R-C(=O)-NH-C(=O)-R) G. Hydrazides (R-C(=O)-NH-NH2) H. Ureas (R-NH-C(=O)-NH2) I. Hydantoins, Uracils, Barbiturates J. Carboxylic Acids (R-C(=O)-OH) 1. Aliphatic and Alicyclic 2. Olefinic 3. Aromatic 4. Amino Acids 5. Salts of Carboxylic Acids K. Esters 1. Aliphatic Esters of Aliphatic Acids 2. Olefinic Esters of Aliphatic Acids 3. Aromatic Esters of Aliphatic Acids 4. Cyclic Esters (Lactones) 5. Chloroformates 6. Carbamates

7. Esters of Phosphorus Acids

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Table of Contents - Carbon NMR I. II. III. IV. V. VI. VII. VIII.

Hydrocarbons Halogenated Hydrocarbons Nitrogen Containing Compounds Silicon Containing Compounds (Except Si-O) Phosphorus Containing Compounds (Except P-O And P(=O)-O) Sulfur Containing Compounds Oxygen Containing Compounds (Except -C(=O)-) Compounds Containing Carbon To Oxygen Double Bonds

I. Hydrocarbons A. Saturated Hydrocarbons 1. Normal Alkanes 2. Branched Alkanes 3. Cyclic Alkanes B. Unsaturated Hydrocarbons 1. Acyclic Alkenes 2. Alkynes C. Aromatic Hydrocarbons 1. Monocyclic (Benzenes) and Polycyclic II. Halogenated Hydrocarbons A. Fluorinated Hydrocarbons 1. Aliphatic 2. Aromatic B. Chlorinated Hydrocarbons 1. Aliphatic 2. Aromatic C. Brominated Hydrocarbons 1. Aliphatic 2. Aromatic D. Iodinated Hydrocarbons 1. Aliphatic 2. Aromatic III. Nitrogen Containing Compounds A. Amines 1. Primary a. Aliphatic b. Aromatic 2. Secondary a. Aliphatic b. Aromatic 3. Tertiary a. Aliphatic b. Aromatic

B. C. D. E. F.

IV. V. VI.

VII.

VIII.

Pyridines Amine Salts Oximes (-CH=N-OH) Quaternary Ammonium Salts Nitriles (-C≡N) 1. Aliphatic 2. Olefinic 3. Aromatic G. Thiocyanates (-S-C≡N) H. Nitro Compounds (-NO2) 1. Aliphatic 2. Aromatic Silicon Containing Compounds (Except Si-O) Phosphorus Containing Compounds (Except P-O and P(=O)-O) Sulfur Containing Compounds A. Sulfides (R-S-R) 1. Aliphatic 2. Aromatic B. Disulfides (R-S-S-R) C. Thiols 1. Aliphatic 2. Aromatic D. Sulfones (R-SO2-R) Oxygen Containing Compounds (Except -C(=O)-) A. Ethers 1. Aliphatic Ethers (R-O-R) 2. Alicyclic Ethers 3. Aromatic Ethers B. Alcohols (R-OH) 1. Primary a. Aliphatic and Alicyclic b. Aromatic 2. Secondary a. Aliphatic and Alicyclic 3. Tertiary a. Aliphatic 4. Phenols Compounds Containing Carbon To Oxygen Double Bonds A. Ketones (R-C(=O)-R) 1. Aliphatic and Alicyclic 2. Aromatic B. Aldehydes (R-C(=O)-H) C. Acid Halides (R-C(=O)-X) D. Anhydrides (R-C(=O)-O-C(=O)-R) E. Amides 1. Primary (R-C(=O)-NH2) 2. Secondary (R-C(=O)-NH-R) 3. Tertiary (R-C(=O)-N-R2) F. Carboxylic Acids (R-C(=O)-OH) 1. Aliphatic and Alicyclic 2. Aromatic G. Esters 1. Aliphatic Esters of Aliphatic Acids

2. Olefinic Esters of Aliphatic Acids 3. Aromatic Esters of Aliphatic Acids

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Table of Contents - MS Coming Soon I. II. III. IV. V. VI. VII. VIII.

Hydrocarbons Halogenated Hydrocarbons Nitrogen Containing Compounds Silicon Containing Compounds (Except Si-O) Phosphorus Containing Compounds (Except P-O And P(=O)-O) Sulfur Containing Compounds Oxygen Containing Compounds (Except -C(=O)-) Compounds Containing Carbon To Oxygen Double Bonds

I. Hydrocarbons A. Saturated Hydrocarbons 1. Normal Alkanes 2. Branched Alkanes 3. Cyclic Alkanes B. Unsaturated Hydrocarbons 1. Acyclic Alkenes 2. Cyclic Alkenes 3. Alkynes C. Aromatic Hydrocarbons 1. Monocyclic (Benzenes) 2. Polycyclic II. Halogenated Hydrocarbons A. Fluorinated Hydrocarbons 1. Aliphatic 2. Aromatic B. Chlorinated Hydrocarbons 1. Aliphatic 2. Olefinic 3. Aromatic C. Brominated Hydrocarbons 1. Aliphatic 2. Olefinic 3. Aromatic D. Iodinated Hydrocarbons 1. Aliphatic and Olefinic 2. Aromatic III. Nitrogen Containing Compounds A. Amines 1. Primary a. Aliphatic and Olefinic b. Aromatic 2. Secondary a. Aliphatic and Olefinic

IV. V. VI.

VII.

b. Aromatic 3. Tertiary a. Aliphatic and Olefinic b. Aromatic B. Pyridines C. Quinolines D. Miscellaneous Nitrogen Heteroaromatics E. Hydrazines F. Amine Salts G. Oximes (-CH=N-OH) H. Hydrazones (-CH=N-NH2) I. Azines (-CH=N-N=CH-) J. Amidines (-N=CH-N) K. Hydroxamic Acids L. Azo Compounds (-N=N-) M. Triazenes (-N=N-NH-) N. Isocyanates (-N=C=O) O. Carbodiimides (-N=C=N-) P. Isothiocyanates (-N=C=S) Q. Nitriles (-C≡N) 1. Aliphatic 2. Olefinic 3. Aromatic R. Cyanamides (=N-C≡N) S. Thiocyanates (-S-C≡N) T. Nitroso Compounds (-N=O) U. N-Nitroso Compounds (=N-N=O) V. Nitrites (-O-N=O) W. Nitro Compounds (-NO2) 1. Aliphatic 2. Aromatic X. N-Nitro-Compounds (=N-NO2) Silicon Containing Compounds (Except Si-O) Phosphorus Containing Compounds (Except P-O and P(=O)-O) Sulfur Containing Compounds A. Sulfides (R-S-R) 1. Aliphatic 2. Heterocyclic 3. Aromatic B. Disulfides (R-S-S-R) C. Thiols 1. Aliphatic 2. Aromatic D. Sulfoxides (R-S(=O)-R) E. Sulfones (R-SO2-R) F. Sulfonyl Halides (R-SO2-X) G. Sulfonic Acids (R-SO2-OH) 1. Sulfonic Acid Salts (R-SO2-O-M) 2. Sulfonic Acid Esters (R-SO2-O-R) 3. Sulfuric Acid Esters (R-O-S(=O)-O-R) H. Thioamides (R-C(=S)-NH2) I. Thioureas (R-NH-C(=S)-NH2) J. Sulfonamides (R-SO2-NH2) K. Sulfamides (R-NH-SO2-NH-R) Oxygen Containing Compounds (Except -C(=O)-) A. Ethers

1. Aliphatic Ethers (R-O-R) 2. Acetals (R-CH-(-O-R)2) 3. Alicyclic Ethers 4. Aromatic Ethers 5. Furans 6. Silicon Ethers (R3-Si-O-R) 7. Phosphorus Ethers ((R-O)3-P) 8. Peroxides (R-O-O-R) B. Alcohols (R-OH) 1. Primary a. Aliphatic and Alicyclic b. Olefinic c. Aromatic d. Heterocyclic 2. Secondary a. Aliphatic and Alicyclic b. Olefinic c. Aromatic 3. Tertiary a. Aliphatic b. Olefinic c. Aromatic 4. Diols 5. Carbohydrates 6. Phenols VIII. Compounds Containing Carbon To Oxygen Double Bonds A. Ketones (R-C(=O)-R) 1. Aliphatic and Alicyclic 2. Olefinic 3. Aromatic 4. α-Diketones and β-Diketones B. Aldehydes (R-C(=O)-H) C. Acid Halides (R-C(=O)-X) D. Anhydrides (R-C(=O)-O-C(=O)-R) E. Amides 1. Primary (R-C(=O)-NH2) 2. Secondary (R-C(=O)-NH-R) 3. Tertiary (R-C(=O)-N-R2) F. Imides (R-C(=O)-NH-C(=O)-R) G. Hydrazides (R-C(=O)-NH-NH2) H. Ureas (R-NH-C(=O)-NH2) I. Hydantoins, Uracils, Barbiturates J. Carboxylic Acids (R-C(=O)-OH) 1. Aliphatic and Alicyclic 2. Olefinic 3. Aromatic 4. Amino Acids 5. Salts of Carboxylic Acids K. Esters 1. Aliphatic Esters of Aliphatic Acids 2. Olefinic Esters of Aliphatic Acids 3. Aliphatic Esters of Olefinic Acids 4. Aromatic Esters of Aliphatic Acids 5. Esters of Aromatic Acids 6. Cyclic Esters (Lactones) 7. Chloroformates 8. Esters of Thio-Acids

9. Carbamates 10. Esters of Phosphorus Acids

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Saturated Hydrocarbons Normal Alkanes 1. C-H stretching vibration: CH3 asymmetric stretching, 2972-2952 cm-1 CH3 symmetric stretching, 2882-2862 cm-1 CH2 asymmetric stretching, 2936-2916 cm-1 CH2 symmetric stretching, 2863-2843 cm-1 2. C-H bending vibration: CH3 asymmetric bending, 1470-1430 cm-1 CH2 asymmetric bending, 1485-1445 cm-1 (overlaps band due to CH3 asymmetric bending) 3. C-H bending vibration: CH3 symmetric bending, 1380-1365 cm-1 (when CH3 is attached to a C atom) 4. C-H wagging vibration: CH2 out-of-plane deformations wagging, 1307-1303 cm-1 (weak) 5. CH2 rocking vibration: (CH2)2 in-plane deformations rocking, 750-740 cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

(CH2)3 in-plane deformations rocking, 740-730 cm-1 (CH2)4 in-plane deformations rocking, 730-725 cm-1 (CH2) ≥ 6 in-plane deformations rocking, 722 cm-1 Splitting of the absorption band occurs in most cases (730 and 720 cm-1) when the long carbon-chain alkane is in the crystalline state (orthorombic or monoclinic form).

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Saturated Hydrocarbons Branched Alkanes 1. C-H stretching vibration: CH3 asymmetric stretching, 2972-2952 cm-1 CH3 symmetric stretching, 2882-2862 cm-1 CH2 asymmetric stretching, 2936-2916 cm-1 CH2 symmetric stretching, 2863-2843 cm-1 2. C-H bending vibration: CH3 asymmetric bending, 1470-1430 cm-1 CH2 asymmetric bending, 1485-1445 cm-1 (overlaps band due to CH3 symmetric bending) 3. C-H bending vibration: -C-C(CH3)-C-C- symmetric bending, 1380-1365 cm-1 (when CH3 is attached to a C atom) -C-C(CH3)-C(CH3)-C-C- symmetric bending, 1380-1365 cm-1 (when CH3 is attached to a C atom) (CH3)2CH- symmetric bending, 1385-1380 cm-1and 1365 cm-1 (two bands of about equal intensity) -C-C(CH3)2-C- symmetric bending,1385-1380 cm-1and 1365 cm-1 (two bands of about equal intensity). (CH3)3C- symmetric bending, 1395-1385 cm-1and 1365 cm-1 (two bands of unequal intensity with the 1365 cm-1 band as the much stronger component of the doublet). 4. Skeletal vibration: -C-C(CH3)-C-C-,1159-1151cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

-C-C(CH3)-C(CH3)-C-C-,1130-1116 cm-1 (CH3)CH-,1175-1165 cm-1 and 1170-1140 cm-1 -C-C(CH3)2-C-,1192-1185 cm-1 (CH3)3C-, 1255-1245 cm-1 and 1250-1200 cm-1 5. C-H rocking vibration: (CH2)2 in-plane deformations rocking, 750-740 cm-1 (CH2)3 in-plane deformations rocking, 740-730 cm-1 (CH2)4 in-plane deformations rocking, 730-725 cm-1 (CH2) ≥ 6 in-plane deformations rocking, 722 cm-1

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Saturated Hydrocarbons Cyclic Alkanes Cyclopropanes 1. C-H stretching vibration: ring CH2 asymmetric stretching, 3100-3072 cm-1 ring CH2 symmetric stretching, 3030-2995 cm-1 2. Ring deformation vibration: ring deformation, 1050-1000 cm-1 3. C-H deformation vibration: CH2 wagging, 860-790 cm-1

Cyclobutanes 1. C-H stretching vibration: ring CH2 asymmetric stretching, 3000-2974 cm-1 ring CH2 symmetric stretching, 2925-2875 cm-1 2. C-H deformation vibration: ring CH2 asymmetric bending, ca 1444 cm-1 3. Ring deformation vibration: ring deformation, 1000-960 cm-1 888-838 cm-1 4. C-H deformation vibration: ring CH2 rocking, 950-900 cm-1

Cyclopentanes 1. C-H stretching vibration: ring CH2 asymmetric stretching, 2960-2952 cm-1 ring CH2 symmetric stretching, 2866-2853 cm-1 2. C-H deformation vibration: ring CH2 asymmetric bending, ca 1455 cm-1 3. Ring deformation vibration: ring deformation, 1000-960 cm-1 4. C-H deformation vibration: ring CH2rocking, 930-890 cm-1

Cyclohexanes 1. C-H stretching vibration: ring CH2 asymmetric stretching, ca 2927 cm-1 ring CH2 symmetric stretching, ca 2854 cm-1 2. C-H deformation vibration: ring CH2 asymmetric bending, ca 1462 cm-1 3. C-H deformation vibration: ring CH2 wagging, ca 1260 cm-1 4. Ring deformation vibration: ring deformation, 1055-1000 cm-1 1000- 952 cm-1 5. C-H deformation vibration: ring CH2 rocking, 890-860 cm-1 6. The spectra of cyclic alkanes of five or more ring carbons show ring CH2 stretching frequencies which overlap those of CH3 and CH2 groups of their alkyl substituents. These frequencies also overlap those of the CH3 and CH2 stretching frequencies of acylic alkanes. When samples of unknown composition are examined for the presence of such ring structures, the absorption bands of their spectra at the C-H stretching region should have the best possible resolution.

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Numerous references cite the spectral region of 2800-2600 cm-1 for obtaining confirmatory evidence of the presence of saturated simple ring structures. Absorption at this region consists of a weak band or bands whose pattern and band locations are helpful in confirming or indicating the presence of these rings. Although such absorption features have a limited diagnostic value, it is most reliable when the absorption occurs in the spectra of simple saturated aliphatic hydrocarbons.

Cycloalkanes

(8, 9, and 10 C atoms)

1 C-H stretching vibration: ring CH2 asymmetric stretching, ca 2930 cm-1 ring CH2 symmetric stretching, ca 2850 cm-1 2. C-H deformation vibration: ring CH2 asymmetric bending, 2 or 3 absorption bands, 1487-1443 cm-1

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Unsaturated Hydrocarbons Acyclic Alkenes Monosubstituted Alkenes (vinyl) 1. C=C stretching vibration: C=C stretching, 1648-1638 cm-1 2. C-H deformation vibration: trans CH wagging, 995-985 cm-1 CH2 wagging, 910-905 cm-1 3. C-H stretching vibration: CH2 asymmetric stretching, 3092-3077 cm-1 CH2 symmetric stretching and CH stretching, 3025-3012 cm-1 4. C-H deformation vibration: CH2 asymmetric bending, 1420-1412 cm-1 5. C-H deformation vibration overtone: overtone of CH2 wagging, 1840-1805 cm-1

Coming Soon! Asymmetric Disubstituted Alkenes (vinylidine) 1. C=C stretching vibration: C=C stretching, 1661-1639 cm-1 2. C-H deformation vibration: CH2 wagging, 895-885 cm-1 3. C-H stretching vibration: CH2 stretching asymmetric, 3100-3077 cm-1 4. C-H deformation vibration overtone: overtone of CH2 wagging, 1792- 1775 cm-1

Symmetric Disubstituted Alkenes (cis) 1. C=C stretching vibration: C=C stretching, 1662- 1631 cm-1 2. C-H deformation vibration: cis CH wagging, 730- 650 cm-1 3. C-H stretching vibration: CH stretching, 3050-3000 cm-1

Symmetric Disubstituted Alkenes (trans) 1. C=C stretching vibration: C=C stretching, ca 1673 cm-1, very weak or absent 2. C-H deformation vibration: trans CH wagging, 980-965 cm-1 3. C-H stretching vibration: CH stretching, 3050-3000 cm-1

Trisubstituted Alkenes 1. C=C stretching vibration: C=C stretching, 1692-1667 cm-1 2. C—H deformation vibration: C-H wagging, 840-790 cm-1 3. C-H stretching vibration: C-H stretching, 3050-2990 cm-1

Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Tetrasubstituted Alkenes 1. C=C stretching vibration: C=C stretching, 1680-1665 cm-1, very weak or absent NOTES: The C=C stretching vibration of molecules which maintain a center of symmetry absorbs very weakly, if at all, in the infrared region and, usually, is difficult to detect. This is true of the trans isomers and the tetrasubstituted C=C linkages. When two or more olefinic groups occur in the hydrocarbon molecule, the infrared absorption spectrum shows the additive and combined absorption of the unsaturated groups. However, if the unsaturated groups are subject to conjugation, the C=C stretching frequency, usually, is lowered and a splitting of the C=C stretching frequency band occurs. Conjugation also intensifies the C=C stretching frequency of trans unsaturated groups.

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Unsaturated Hydrocarbons Cyclic Alkenes Endocyclic C=C Endocyclic C=C corresponds to cis symmetrically disubstituted C=C of acyclic alkenes. 1. C=C stretching, vibration: C=C stretching, near 1650 cm-1 (except cyclobutene, 1560 cm-1 and cyclopentene, 1611 cm-1) 2. C-H deformation vibration: CH wagging, 730- 650 cm-1 3. C-H stretching vibration: CH stretching, 3075- 3010 cm-1 (usually two bands, asymmetric stretching and symmetric stretching for 4, 6, 7, and 8 membered rings)

1- substituted endocyclic C=C 1- substituted endocyclic C=C corresponds to trisubstituted acyclic alkenes. 1. C=C stretching vibration: C=C stretching, near 1650 cm-1 (frequency raised) 2. C-H deformation vibration: CH wagging, 840-790 cm-1 3. C-H stretching vibration: CH stretching, near 3000 cm-1

1.2- disubstituted endocyclic C=C 1. C=C stretching vibration: C=C stretching, 1690-1670 cm-1 (4, 5, and 6 membered rings)

Exocyclic C=CH2 Exocyclic C=CH2 corresponds to the asymmetrically disubstituted C=C of acyclic alkenes (vinylidine). 1. C=C stretching,1678-1650 cm-1 (4, 5, and 6 membered rings) 2. C-H deformation vibration: =CH2 wagging, 895-885 cm-1 3. C-H stretching vibration: =CH2 stretching, near 3050 cm-1 NOTES: The C=C stretching frequency of both the endocyclic HC=CH and the exocyclic C=CH2 is sensitive to ring strain. As the ring size decreases from 6 to 4 members, the C=C stretching frequency of the endocyclic HC=CH is lowered. However, for the C=C stretching frequency of exocyclic C=CH2, a gradual increase in the C=C stretching frequency occurs as the ring gets smaller. Substitution of methyl groups for the hydrogens of the endocyclic HC=CH and the exocyclic C=CH2 cause an increase in the C=C stretching frequency. When two or more C=C groups occur in the hydrocarbon molecule, the infrared absorption spectrum shows the additive and combined absorption effects of the unsaturated groups. If such groups are subject to conjugation, the C=C stretching frequency is lowered and a splitting of the C=C stretching frequency band occurs.

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

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Unsaturated Hydrocarbons Alkynes Monosubstituted Alkynes (RC≡CH) 1. C≡C stretching vibration: C≡C stretching, 2140-2100 cm-1 2. C-H stretching vibration: ≡CH bending, ca 3300 cm-1 3. C-H deformation vibration: ≡CH bending, 642-615 cm-1 4. C-H deformation vibration overtone: overtone of ≡CH deformation, 1260-1245 cm-1

Disubstituted Alkynes (RC≡CR') 1. C≡C stretching vibration: C≡C stretching, 2260-2190 cm-1 (unconjugated) NOTES: Although the intensity of the absorption band caused by the C≡C stretching vibration is variable, it is strongest when the alkyne group is monosubstituted. When this group is disubstituted in open chain compounds, the intensity of the C≡C stretching vibration band diminishes as its position in the molecule tends to establish a pseudo center of symmetry. In some instances this band is too weak to be detected and, thus, its absence in the spectrum does not, necessarily, establish proof of the absence of this linkage.

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Occasionally, the spectra of disubstituted alkynes show two or more bands at the C≡C stretching region. Conjugation with olefinic double bonds or aromatic rings tend to slightly increase the intensity of the C≡C stretching vibration band and shift it to a lower frequency.

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Unsaturated Hydrocarbons Monocyclic Aromatic Benzene 1. C-C stretching vibration: C-C stretching, 1485 cm-1 2. C-H deformation vibration of ring hydrogens: ring CH wagging, 670 cm-1 (6 adjacent hydrogens) 3. C-H stretching vibration of ring hydrogens: CH stretching, 3100-3000 cm-1 (3 bands one of which is a fundamental vibration) 4. C-H deformation vibration of ring hydrogens: CH in-plane deformation, 1037 cm-1

Monosubstituted Benzene 1. C-C stretching vibration: C-C stretching, ca 1600 cm-1and 1590 cm-1 (weak shoulder band) ca 1500 cm-1and 1450 cm-1 (coalesces with CH3 and CH2 asymmetric bending of alkyl substituents) 2. C-H deformation vibration of ring hydrogens: ring CH wagging, 770-730 cm-1 (5 adjacent hydrogens) 3. Ring deformation vibration: ring deformation, 710- 695 cm-1 4. Overtone and combination bands of CH deformation vibrations: overtone and combination bands of CH wagging, 2000 -1660 cm-1 (characteristic pattern) 5. C-H stretching vibration of ring hydrogens: CH stretching, 3100-3000 cm-1 (3-5 bands)

Disubstituted Benzene 1. C-C stretching vibration: 1,2-disubstituted, C-C stretching, ca 1609 cm-1 and 1575 cm-1 (weak) ca 1490 cm-1 and 1445 cm-1 * 1,3-disubstituted, C-C stretching, ca 1610 cm-1 and 1590 cm-1 (weak) ca 1500 cm-1 and 1447 cm-1 * 1,4-disubstituted, C-C stretching, ca 1620 cm-1 and 1571 cm-1 (weak) ca 1512 cm-1 and 1450 cm-1 * * Generally overlaps the band due to CH3 and CH2 asymmetric bending vibration. 2. C-H deformation vibration of ring hydrogens: 1,2-disubstituted, CH wagging, 770-730 cm-1 (4 adjacent hydrogens) 1,3-disubstituted, CH wagging, 810-750 cm-1 (3 adjacent hydrogens) 900-860 cm-1 (isolated hydrogen) 1,4-disubstituted, CH wagging, 860- 800 cm-1 (2 adjacent hydrogens) 3. Ring deformation vibration: 1,2-disubstituted, ring deformation, 730-690 cm-1 * 1,3-disubstituted, ring deformation, 710-690 cm-1 1,4-disubstituted, ring deformation, 730-690 cm-1 * *Only present, as a weak band, when the two substituents are different. 4. Overtone and combination bands of CH deformation vibrations: overtone and combination bands of CH wagging, 2000 - 1660 cm-1 * * Each type of substitution has a unique pattern of bands. 5. C-H stretching vibration of ring hydrogens:

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

CH stretching, 3100-3000 cm-1 (3-5 bands)

Trisubstituted Benzene 1. C-C stretching vibration: 1,2,3-trisubstituted, C-C stretching, generally 4 bands in the range, 1,2,4-trisubstituted, C-C stretching, 1650-1450 cm-1, with the main bands 1,3,5-trisubstituted, C-C stretching, occurring ca 1600 and 1500 cm-1 2. C-H deformation vibration of ring hydrogens: 1,2,3-trisubstituted, CH wagging, 810-750 cm-1 (3 adjacent hydrogens) 1,2,4-trisubstituted, CH wagging, 860-800 cm-1 (2 adjacent hydrogens) 885-860 cm-1 (isolated hydrogen) 1,3,5-trisubstituted, CH wagging, 874-835 cm-1 (isolated hydrogen) 3. Ring deformation vibration: 1,2,3-trisubstituted, ring deformation, 725-680 cm-1 1,2,4-trisubstituted, ring deformation, 750-700 cm-1 (very weak or none) 1,3,5-trisubstituted, ring deformation, 730-675 cm-1 4. Overtone and combination bands of CH deformation vibrations: overtone and combination bands of CH wagging, 2000-1660 cm-1 * * Each type of substitution has an unique pattern of bands. 5. C-H stretching vibration of ring hydrogens: CH stretching, 3100-3000 cm-1

Tetrasubstituted Benzene 1. C-C stretching vibration: 1,2,3,4-tetrasubstituted, C-C stretching, main bands ca 1600 and 1500 cm-1 1,2,3,5-tetrasubstituted, C-C stretching, main bands ca 1600 and 1500 cm-1 1,2,4,5-tetrasubstituted, C-C stretching, main bands ca 1600 and 1500 cm-1 2. C-H deformation of ring hydrogens: 1,2,3,4-tetrasubstituted, CH wagging, 860-800 cm-1 (2 adjacent hydrogens) 1,2,3,5-tetrasubstituted, CH wagging, 865-810 cm-1 (isolated hydrogen) 1,2,4,5-tetrasubstituted, CH wagging, 860-800 cm-1 (isolated hydrogen) 3. Ring deformation vibration: 1,2,3,4-tetrasubstituted, ring deformation, no band (750-675 cm-1) 1,2,3,5-tetrasubstituted, ring deformation, 730-675 cm-1 1,2,4,5-tetrasubstituted, ring deformation, no band (750-675 cm-1) 4. Overtone and combination of CH deformation vibrations: overtone and combination bands of CH wagging, 2000-1600 cm-1 * * Each type of substitution has an unique pattern of bands. 5. C-H stretching vibration of ring hydrogens: CH stretching, 3100-3000 cm-1 (usually 1 band ca 3000 cm-1)

Pentasubstituted Benzene 1. C-C stretching vibration: C-C stretching, near 1600 and 1500 cm-1 2. C-H deformation of ring hydrogens: CH wagging, ca 860 cm-1 3. Ring deformation vibration: ring deformation, 710-695 cm-1 (weak) 4. Overtone and combination bands of CH deformation vibrations: overtone and combination bands of CH wagging 2000-1600 cm-1 * * Unique pattern of bands. 5. C-H stretching vibration of ring hydrogens: CH stretching, ca 3000 cm-1 NOTES: Absorption bands occurring in the region of 1620-1450 cm-1 of the spectra of substituted benzenes are subject to small changes in location and significant changes in intensity. Two of the actors that contribute to these changes are molecular symmetry and ring substituents that have a strong electrometric effect.

When a substituent of a substituted benzene contains a double bond linkage or a lone electron pair (as in the instance of a halogen) that is conjugated with the benzene ring, the absorption bands related to the substituted benzene (see previously listed data) are altered. Generally, the absorption occurring in the region of 1620-1540 cm-1 is resolved as a distinct doublet with an appreciable enhancement of the band near 1580 cm-1. In the majority of cases of conjugation involving the ring and a C=O linkage or a nitro group, the C-H deformation vibration of ring hydrogens are also disturbed. As a consequence, the previously assigned correlation and absorption band locations due to ring CH wag at the region of 900-690 cm-1 lose their diagnostic value. Those absorption bands which occur in this region of the spectra of such conjugated benzenes are of doubtful value for indicating a particular pattern of ring substitution.

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Unsaturated Hydrocarbons Monocyclic and Polycyclic Aromatics Benzene 1. C-C stretching vibration: C-C stretching, 1485 cm-1 2. C-H deformation vibration of ring hydrogens: ring CH wagging, 670 cm-1 (6 adjacent hydrogens) 3. C-H stretching vibration of ring hydrogens: CH stretching, 3100-3000 cm-1 (3 bands one of which is a fundamental vibration) 4. C-H deformation vibration of ring hydrogens: CH in-plane deformation, 1037 cm-1

Monosubstituted Benzene 1. C-C stretching vibration: C-C stretching, ca 1600 cm-1and 1590 cm-1 (weak shoulder band) ca 1500 cm-1and 1450 cm-1 (coalesces with CH3 and CH2 asymmetric bending of alkyl substituents) 2. C-H deformation vibration of ring hydrogens: ring CH wagging, 770-730 cm-1 (5 adjacent hydrogens) 3. Ring deformation vibration: ring deformation, 710- 695 cm-1 4. Overtone and combination bands of CH deformation vibrations: overtone and combination bands of CH wagging, 2000 -1660 cm-1 (characteristic pattern) 5. C-H stretching vibration of ring hydrogens: CH stretching, 3100-3000 cm-1 (3-5 bands)

Disubstituted Benzene 1. C-C stretching vibration: 1,2-disubstituted, C-C stretching, ca 1609 cm-1 and 1575 cm-1 (weak) ca 1490 cm-1 and 1445 cm-1 * 1,3-disubstituted, C-C stretching, ca 1610 cm-1 and 1590 cm-1 (weak) ca 1500 cm-1 and 1447 cm-1 * 1,4-disubstituted, C-C stretching, ca 1620 cm-1 and 1571 cm-1 (weak) ca 1512 cm-1 and 1450 cm-1 * * Generally overlaps the band due to CH3 and CH2 asymmetric bending vibration. 2. C-H deformation vibration of ring hydrogens: 1,2-disubstituted, CH wagging, 770-730 cm-1 (4 adjacent hydrogens) 1,3-disubstituted, CH wagging, 810-750 cm-1 (3 adjacent hydrogens) 900-860 cm-1 (isolated hydrogen) 1,4-disubstituted, CH wagging, 860- 800 cm-1 (2 adjacent hydrogens) 3. Ring deformation vibration: 1,2-disubstituted, ring deformation, 730-690 cm-1 * 1,3-disubstituted, ring deformation, 710-690 cm-1 1,4-disubstituted, ring deformation, 730-690 cm-1 * *Only present, as a weak band, when the two substituents are different. 4. Overtone and combination bands of CH deformation vibrations: overtone and combination bands of CH wagging, 2000 - 1660 cm-1 * * Each type of substitution has a unique pattern of bands. 5. C-H stretching vibration of ring hydrogens: CH stretching, 3100-3000 cm-1 (3-5 bands)

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Trisubstituted Benzene 1. C-C stretching vibration: 1,2,3-trisubstituted, C-C stretching, generally 4 bands in the range, 1,2,4-trisubstituted, C-C stretching, 1650-1450 cm-1, with the main bands 1,3,5-trisubstituted, C-C stretching, occurring ca 1600 and 1500 cm-1 2. C-H deformation vibration of ring hydrogens: 1,2,3-trisubstituted, CH wagging, 810-750 cm-1 (3 adjacent hydrogens) 1,2,4-trisubstituted, CH wagging, 860-800 cm-1 (2 adjacent hydrogens) 885-860 cm-1 (isolated hydrogen) 1,3,5-trisubstituted, CH wagging, 874-835 cm-1 (isolated hydrogen) 3. Ring deformation vibration: 1,2,3-trisubstituted, ring deformation, 725-680 cm-1 1,2,4-trisubstituted, ring deformation, 750-700 cm-1 (very weak or none) 1,3,5-trisubstituted, ring deformation, 730-675 cm-1 4. Overtone and combination bands of CH deformation vibrations: overtone and combination bands of CH wagging, 2000-1660 cm-1 * * Each type of substitution has an unique pattern of bands. 5. C-H stretching vibration of ring hydrogens: CH stretching, 3100-3000 cm-1

Tetrasubstituted Benzene 1. C-C stretching vibration: 1,2,3,4-tetrasubstituted, C-C stretching, main bands ca 1600 and 1500 cm-1 1,2,3,5-tetrasubstituted, C-C stretching, main bands ca 1600 and 1500 cm-1 1,2,4,5-tetrasubstituted, C-C stretching, main bands ca 1600 and 1500 cm-1 2. C-H deformation of ring hydrogens: 1,2,3,4-tetrasubstituted, CH wagging, 860-800 cm-1 (2 adjacent hydrogens) 1,2,3,5-tetrasubstituted, CH wagging, 865-810 cm-1 (isolated hydrogen) 1,2,4,5-tetrasubstituted, CH wagging, 860-800 cm-1 (isolated hydrogen) 3. Ring deformation vibration: 1,2,3,4-tetrasubstituted, ring deformation, no band (750-675 cm-1) 1,2,3,5-tetrasubstituted, ring deformation, 730-675 cm-1 1,2,4,5-tetrasubstituted, ring deformation, no band (750-675 cm-1) 4. Overtone and combination of CH deformation vibrations: overtone and combination bands of CH wagging, 2000-1600 cm-1 * * Each type of substitution has an unique pattern of bands. 5. C-H stretching vibration of ring hydrogens: CH stretching, 3100-3000 cm-1 (usually 1 band ca 3000 cm-1)

Pentasubstituted Benzene 1. C-C stretching vibration: C-C stretching, near 1600 and 1500 cm-1 2. C-H deformation of ring hydrogens: CH wagging, ca 860 cm-1 3. Ring deformation vibration: ring deformation, 710-695 cm-1 (weak) 4. Overtone and combination bands of CH deformation vibrations: overtone and combination bands of CH wagging 2000-1600 cm-1 * * Unique pattern of bands. 5. C-H stretching vibration of ring hydrogens: CH stretching, ca 3000 cm-1 NOTES: Absorption bands occurring in the region of 1620-1450 cm-1 of the spectra of substituted benzenes are subject to small changes in location and significant changes in intensity. Two of the actors that contribute to these changes are molecular symmetry and ring substituents that have a strong electrometric effect. When a substituent of a substituted benzene contains a double bond linkage or a lone electron pair (as in the instance of a halogen) that is conjugated with the benzene ring, the absorption bands related to the substituted benzene (see previously listed data) are altered. Generally, the absorption

occurring in the region of 1620-1540 cm-1 is resolved as a distinct doublet with an appreciable enhancement of the band near 1580 cm-1. In the majority of cases of conjugation involving the ring and a C=O linkage or a nitro group, the C-H deformation vibration of ring hydrogens are also disturbed. As a consequence, the previously assigned correlation and absorption band locations due to ring CH wag at the region of 900-690 cm-1 lose their diagnostic value. Those absorption bands which occur in this region of the spectra of such conjugated benzenes are of doubtful value for indicating a particular pattern of ring substitution.

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Halogenated Hydrocarbons Fluorinated Fluorinated Aliphatic Hydrocarbons 1. C-F stretching vibration: C-F stretching, (range) 1400-1000 cm-1 (intense absorption) C-F stretching, 1100-1000 cm-1 C-F stretching, (polyfluorinated) 1400-1000 cm-1 (two or more bands)

Fluorinated Aromatic Hydrocarbons 1. C-F stretching vibration: C-F stretching, (usually) 1300-1200 cm-1 (intense absorption)

General Note on Halogenated Hydrocarbons The detection of carbon to halogen bonds is not readily accomplished through the examination of the infrared absorption spectra of this class of compounds. The difficulty of locating and recognizing absorption bands that arise from the C-X bonds is attributed to the following factors:

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

1. A variety of C-X bonds exist. 2. The C-X bonds are subject to appreciable alteration in vibrational frequency through interaction with neighboring groups. 3. Different conformational isomers have different stretching frequencies. 4. Equatorial and axial C-X bonds of ring structures have different stretching frequencies. 5. Multiple absorption bands related to the C-X bonds usually occur in the infrared spectrum. As a consequence of these factors, the C-X bonds do not always possess a constant vibrational frequency nor do they always have unique absorption band features. A more reliable means of detecting and identifying halogen substituents consists of procedures for elemental analysis. Whenever feasible, the sample should be examined by these procedures prior to its examination by infrared spectroscopy. A knowledge of the kind of halogen present in the sample simplifies locating and identifying those absorption bands that are related to the C-X bond.

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Halogenated Hydrocarbons Fluorinated Fluorinated Aliphatic Hydrocarbons 1. C-F stretching vibration: C-F stretching, (range) 1400-1000 cm-1 (intense absorption) C-F stretching, 1100-1000 cm-1 C-F stretching, (polyfluorinated) 1400-1000 cm-1 (two or more bands)

Fluorinated Aromatic Hydrocarbons 1. C-F stretching vibration: C-F stretching, (usually) 1300-1200 cm-1 (intense absorption)

General Note on Halogenated Hydrocarbons The detection of carbon to halogen bonds is not readily accomplished through the examination of the infrared absorption spectra of this class of compounds. The difficulty of locating and recognizing absorption bands that arise from the C-X bonds is attributed to the following factors:

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

1. A variety of C-X bonds exist. 2. The C-X bonds are subject to appreciable alteration in vibrational frequency through interaction with neighboring groups. 3. Different conformational isomers have different stretching frequencies. 4. Equatorial and axial C-X bonds of ring structures have different stretching frequencies. 5. Multiple absorption bands related to the C-X bonds usually occur in the infrared spectrum. As a consequence of these factors, the C-X bonds do not always possess a constant vibrational frequency nor do they always have unique absorption band features. A more reliable means of detecting and identifying halogen substituents consists of procedures for elemental analysis. Whenever feasible, the sample should be examined by these procedures prior to its examination by infrared spectroscopy. A knowledge of the kind of halogen present in the sample simplifies locating and identifying those absorption bands that are related to the C-X bond.

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Halogenated Hydrocarbons Chlorinated Chlorinated Aliphatic Hydrocarbons 1. C-Cl stretching vibration: C-CI stretching, (range) 800-600 cm-1 (intense absorption) C-Cl stretching, (liquid consisting of more than one conformational isomer) 800-600 cm-1 (intense absorption) C-Cl stretching, (trans isomer) 750-700 cm-1 C-Cl stretching, (gauche isomer) near 650 cm-1 C-Cl stretching, (cyclohexane rings); equatorial 800-700 cm-1 axial 710-650 cm-1

Chlorinated Aromatic Hydrocarbons 1. C-Cl stretching vibration C-Cl stretching, near 1050 cm-1 (questionable) 2. Cl sensitive vibrational modes 1200-1000 cm-1 (strong multiple bands)

General Note on Halogenated Hydrocarbons The detection of carbon to halogen bonds is not readily accomplished through the examination of the infrared absorption spectra of this class of compounds. The difficulty of locating and recognizing absorption bands that arise from the C-X bonds is attributed to the following factors:

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

1. A variety of C-X bonds exist. 2. The C-X bonds are subject to appreciable alteration in vibrational frequency through interaction with neighboring groups. 3. Different conformational isomers have different stretching frequencies. 4. Equatorial and axial C-X bonds of ring structures have different stretching frequencies. 5. Multiple absorption bands related to the C-X bonds usually occur in the infrared spectrum. As a consequence of these factors, the C-X bonds do not always possess a constant vibrational frequency nor do they always have unique absorption band features. A more reliable means of detecting and identifying halogen substituents consists of procedures for elemental analysis. Whenever feasible, the sample should be examined by these procedures prior to its examination by infrared spectroscopy. A knowledge of the kind of halogen present in the sample simplifies locating and identifying those absorption bands that are related to the C-X bond.

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Halogenated Hydrocarbons Chlorinated Chlorinated Aliphatic Hydrocarbons 1. C-Cl stretching vibration: C-CI stretching, (range) 800-600 cm-1 (intense absorption) C-Cl stretching, (liquid consisting of more than one conformational isomer) 800-600 cm-1 (intense absorption) C-Cl stretching, (trans isomer) 750-700 cm-1 C-Cl stretching, (gauche isomer) near 650 cm-1 C-Cl stretching, (cyclohexane rings); equatorial 800-700 cm-1 axial 710-650 cm-1

Chlorinated Aromatic Hydrocarbons 1. C-Cl stretching vibration C-Cl stretching, near 1050 cm-1 (questionable) 2. Cl sensitive vibrational modes 1200-1000 cm-1 (strong multiple bands)

Coming Soon! General Note on Halogenated Hydrocarbons The detection of carbon to halogen bonds is not readily accomplished through the examination of the infrared absorption spectra of this class of compounds. The difficulty of locating and recognizing absorption bands that arise from the C-X bonds is attributed to the following factors:

Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

1. A variety of C-X bonds exist. 2. The C-X bonds are subject to appreciable alteration in vibrational frequency through interaction with neighboring groups. 3. Different conformational isomers have different stretching frequencies. 4. Equatorial and axial C-X bonds of ring structures have different stretching frequencies. 5. Multiple absorption bands related to the C-X bonds usually occur in the infrared spectrum. As a consequence of these factors, the C-X bonds do not always possess a constant vibrational frequency nor do they always have unique absorption band features. A more reliable means of detecting and identifying halogen substituents consists of procedures for elemental analysis. Whenever feasible, the sample should be examined by these procedures prior to its examination by infrared spectroscopy. A knowledge of the kind of halogen present in the sample simplifies locating and identifying those absorption bands that are related to the C-X bond.

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Halogenated Hydrocarbons Chlorinated Chlorinated Aliphatic Hydrocarbons 1. C-Cl stretching vibration: C-CI stretching, (range) 800-600 cm-1 (intense absorption) C-Cl stretching, (liquid consisting of more than one conformational isomer) 800-600 cm-1 (intense absorption) C-Cl stretching, (trans isomer) 750-700 cm-1 C-Cl stretching, (gauche isomer) near 650 cm-1 C-Cl stretching, (cyclohexane rings); equatorial 800-700 cm-1 axial 710-650 cm-1

Chlorinated Aromatic Hydrocarbons 1. C-Cl stretching vibration C-Cl stretching, near 1050 cm-1 (questionable) 2. Cl sensitive vibrational modes 1200-1000 cm-1 (strong multiple bands)

General Note on Halogenated Hydrocarbons The detection of carbon to halogen bonds is not readily accomplished through the examination of the infrared absorption spectra of this class of compounds. The difficulty of locating and recognizing absorption bands that arise from the C-X bonds is attributed to the following factors:

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

1. A variety of C-X bonds exist. 2. The C-X bonds are subject to appreciable alteration in vibrational frequency through interaction with neighboring groups. 3. Different conformational isomers have different stretching frequencies. 4. Equatorial and axial C-X bonds of ring structures have different stretching frequencies. 5. Multiple absorption bands related to the C-X bonds usually occur in the infrared spectrum. As a consequence of these factors, the C-X bonds do not always possess a constant vibrational frequency nor do they always have unique absorption band features. A more reliable means of detecting and identifying halogen substituents consists of procedures for elemental analysis. Whenever feasible, the sample should be examined by these procedures prior to its examination by infrared spectroscopy. A knowledge of the kind of halogen present in the sample simplifies locating and identifying those absorption bands that are related to the C-X bond.

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Halogenated Hydrocarbons Brominated Brominated Aliphatic Hydrocarbons 1. C-Br stretching vibration: C-Br stretching, (range) 700-500 cm-1 (intense absorption) C-Br stretching, (liquid consisting of more than one conformations) 700-500 cm-1 (strong multiple bands) C-Br stretching, (trans isomer) near 650 cm-1 C-Br stretching, (gauche isomer) near 650 cm-1 C-Br stretching, (cyclohexane rings) equatorial near 700 cm-1 axial near 650 cm-1

Brominated Aromatic Hydrocarbons 1. C-Br stretching vibration: C-Br stretching, ca 1050 cm-1 (questionable) 2. Br sensitive vibrational modes 1200-1000 cm-1 (strong multiple bands) (same as chlorinated aromatic hydrocarbons)

General Note on Halogenated Hydrocarbons The detection of carbon to halogen bonds is not readily accomplished through the examination of the infrared absorption spectra of this class of compounds. The difficulty of locating and recognizing absorption bands that arise from the CX bonds is attributed to the following factors: 1. A variety of C-X bonds exist. 2. The C-X bonds are subject to appreciable alteration in vibrational frequency through interaction with neighboring groups. 3. Different conformational isomers have different stretching frequencies. 4. Equatorial and axial C-X bonds of ring structures have different stretching frequencies. 5. Multiple absorption bands related to the C-X bonds usually occur in the infrared spectrum. As a consequence of these factors, the C-X bonds do not always possess a constant vibrational frequency nor do they always have unique absorption band features. A more reliable means of detecting and identifying halogen substituents consists of procedures for elemental analysis. Whenever feasible, the sample should be examined by these procedures prior to its examination by infrared spectroscopy.

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

A knowledge of the kind of halogen present in the sample simplifies locating and identifying those absorption bands that are related to the C-X bond.

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Halogenated Hydrocarbons Brominated Brominated Aliphatic Hydrocarbons 1. C-Br stretching vibration: C-Br stretching, (range) 700-500 cm-1 (intense absorption) C-Br stretching, (liquid consisting of more than one conformations) 700-500 cm-1 (strong multiple bands) C-Br stretching, (trans isomer) near 650 cm-1 C-Br stretching, (gauche isomer) near 650 cm-1 C-Br stretching, (cyclohexane rings) equatorial near 700 cm-1 axial near 650 cm-1

Brominated Aromatic Hydrocarbons 1. C-Br stretching vibration: C-Br stretching, ca 1050 cm-1 (questionable) 2. Br sensitive vibrational modes 1200-1000 cm-1 (strong multiple bands) (same as chlorinated aromatic hydrocarbons)

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

General Note on Halogenated Hydrocarbons The detection of carbon to halogen bonds is not readily accomplished through the examination of the infrared absorption spectra of this class of compounds. The difficulty of locating and recognizing absorption bands that arise from the C-X bonds is attributed to the following factors: 1. A variety of C-X bonds exist. 2. The C-X bonds are subject to appreciable alteration in vibrational frequency through interaction with neighboring groups. 3. Different conformational isomers have different stretching frequencies. 4. Equatorial and axial C-X bonds of ring structures have different stretching frequencies. 5. Multiple absorption bands related to the C-X bonds usually occur in the infrared spectrum. As a consequence of these factors, the C-X bonds do not always possess a constant vibrational frequency nor do they always have unique absorption band features. A more reliable means of detecting and identifying halogen substituents consists of procedures for elemental analysis. Whenever feasible, the sample should be examined by these procedures prior to its examination by infrared spectroscopy. A knowledge of the kind of halogen present in the sample simplifies locating and identifying those absorption bands that are related to the C-X bond.

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Halogenated Hydrocarbons Brominated Brominated Aliphatic Hydrocarbons 1. C-Br stretching vibration: C-Br stretching, (range) 700-500 cm-1 (intense absorption) C-Br stretching, (liquid consisting of more than one conformations) 700-500 cm-1 (strong multiple bands) C-Br stretching, (trans isomer) near 650 cm-1 C-Br stretching, (gauche isomer) near 650 cm-1 C-Br stretching, (cyclohexane rings) equatorial near 700 cm-1 axial near 650 cm-1

Brominated Aromatic Hydrocarbons 1. C-Br stretching vibration: C-Br stretching, ca 1050 cm-1 (questionable) 2. Br sensitive vibrational modes 1200-1000 cm-1 (strong multiple bands) (same as chlorinated aromatic hydrocarbons)

General Note on Halogenated Hydrocarbons The detection of carbon to halogen bonds is not readily accomplished through the examination of the infrared absorption spectra of this class of compounds. The difficulty of locating and recognizing absorption bands that arise from the CX bonds is attributed to the following factors: 1. A variety of C-X bonds exist. 2. The C-X bonds are subject to appreciable alteration in vibrational frequency through interaction with neighboring groups. 3. Different conformational isomers have different stretching frequencies. 4. Equatorial and axial C-X bonds of ring structures have different stretching frequencies. 5. Multiple absorption bands related to the C-X bonds usually occur in the infrared spectrum. As a consequence of these factors, the C-X bonds do not always possess a constant vibrational frequency nor do they always have unique absorption band features. A more reliable means of detecting and identifying halogen substituents consists of procedures for elemental analysis. Whenever feasible, the sample should be examined by these procedures prior to its examination by infrared spectroscopy.

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

A knowledge of the kind of halogen present in the sample simplifies locating and identifying those absorption bands that are related to the C-X bond.

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Halogenated Hydrocarbons Iodinated Iodinated Aliphatic Hydrocarbons 1. C-l stretching vibration: C-I stretching, (range) 620-490 cm-1(intense absorption) C-I stretching, (liquid consisting of more than one conformational isomer) 620-490 cm-1(strong multiple bands) C-I stretching, (trans isomer) near 600 cm-1 C-I stretching, (gauche isomer) near 500 cm-1

lodinated Aromatic Hydrocarbons 1. I sensitive vibrational modes 1200-1000 cm-1 (same as chlorinated and brominated aromatic hydrocarbons)

Coming Soon! General Note on Halogenated Hydrocarbons The detection of carbon to halogen bonds is not readily accomplished through the examination of the infrared absorption spectra of this class of compounds. The difficulty of locating and recognizing absorption bands that arise from the C-X bonds is attributed to the following factors:

Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

1. A variety of C-X bonds exist. 2. The C-X bonds are subject to appreciable alteration in vibrational frequency through interaction with neighboring groups. 3. Different conformational isomers have different stretching frequencies. 4. Equatorial and axial C-X bonds of ring structures have different stretching frequencies. 5. Multiple absorption bands related to the C-X bonds usually occur in the infrared spectrum. As a consequence of these factors, the C-X bonds do not always possess a constant vibrational frequency nor do they always have unique absorption band features. A more reliable means of detecting and identifying halogen substituents consists of procedures for elemental analysis. Whenever feasible, the sample should be examined by these procedures prior to its examination by infrared spectroscopy. A knowledge of the kind of halogen present in the sample simplifies locating and identifying those absorption bands that are related to the C-X bond.

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Halogenated Hydrocarbons Iodinated Iodinated Aliphatic Hydrocarbons 1. C-l stretching vibration: C-I stretching, (range) 620-490 cm-1(intense absorption) C-I stretching, (liquid consisting of more than one conformational isomer) 620-490 cm-1(strong multiple bands) C-I stretching, (trans isomer) near 600 cm-1 C-I stretching, (gauche isomer) near 500 cm-1

lodinated Aromatic Hydrocarbons 1. I sensitive vibrational modes 1200-1000 cm-1 (same as chlorinated and brominated aromatic hydrocarbons)

Coming Soon! General Note on Halogenated Hydrocarbons The detection of carbon to halogen bonds is not readily accomplished through the examination of the infrared absorption spectra of this class of compounds. The difficulty of locating and recognizing absorption bands that arise from the C-X bonds is attributed to the following factors:

Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

1. A variety of C-X bonds exist. 2. The C-X bonds are subject to appreciable alteration in vibrational frequency through interaction with neighboring groups. 3. Different conformational isomers have different stretching frequencies. 4. Equatorial and axial C-X bonds of ring structures have different stretching frequencies. 5. Multiple absorption bands related to the C-X bonds usually occur in the infrared spectrum. As a consequence of these factors, the C-X bonds do not always possess a constant vibrational frequency nor do they always have unique absorption band features. A more reliable means of detecting and identifying halogen substituents consists of procedures for elemental analysis. Whenever feasible, the sample should be examined by these procedures prior to its examination by infrared spectroscopy. A knowledge of the kind of halogen present in the sample simplifies locating and identifying those absorption bands that are related to the C-X bond.

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Primary Amines Aliphatic Primary Amines 1. N-H stretching vibration: NH2 asymmetric stretching, ca 3500 cm-1 NH2 symmetric stretching, ca 3400 cm-1 2. N-H deformation vibration, in-plane: NH2 in-plane deformation, 1650-1590 cm-1 (broad medium strong) 3. N-H deformation vibration, out of plane: NH2 out-of-plane deformation, 900-650 cm-1 (broad strong) 4. C-N stretching vibration: C-N stretching, 1220-1020 cm-1

Aromatic Primary Amines, N atom attached to C atom of side chain Absorption features are the same as those listed for primary amines, but overlay the absorption features of the aromatic ring.

Aromatic Primary Amines, N atom attached to C atom of aromatic ring

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1. N-H stretching vibration: NH2 asymmetric stretching, ca 3500 cm-1 NH2 symmetric stretching, ca 3400 cm-1 2. N-H deformation vibration, in-plane: NH2 in-plane deformation, 1650-1590 cm-1 (in many instances, very strong and characteristic of N atom attached to C atom of aromatic ring) 3. N-H deformation vibration, out-of-plane: NH2 out-of-plane deformation, 900-650 cm-1 (usually masked by absorption features of aromatic ring) 4. C-N stretching vibration: C-N stretching, 1340-1250 cm-1

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Primary Amines Aliphatic Primary Amines 1. N-H stretching vibration: NH2 asymmetric stretching, ca 3500 cm-1 NH2 symmetric stretching, ca 3400 cm-1 2. N-H deformation vibration, in-plane: NH2 in-plane deformation, 1650-1590 cm-1 (broad medium strong) 3. N-H deformation vibration, out of plane: NH2 out-of-plane deformation, 900-650 cm-1 (broad strong) 4. C-N stretching vibration: C-N stretching, 1220-1020 cm-1

Aromatic Primary Amines, N atom attached to C atom of side chain Absorption features are the same as those listed for primary amines, but overlay the absorption features of the aromatic ring.

Aromatic Primary Amines, N atom attached to C atom of aromatic ring 1. N-H stretching vibration: NH2 asymmetric stretching, ca 3500 cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

NH2 symmetric stretching, ca 3400 cm-1 2. N-H deformation vibration, in-plane: NH2 in-plane deformation, 1650-1590 cm-1 (in many instances, very strong and characteristic of N atom attached to C atom of aromatic ring) 3. N-H deformation vibration, out-of-plane: NH2 out-of-plane deformation, 900-650 cm-1 (usually masked by absorption features of aromatic ring) 4. C-N stretching vibration: C-N stretching, 1340-1250 cm-1

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Secondary Aliphatic Amines Aliphatic Amines 1. N-H stretching vibration: NH stretching, near 3300 cm-1 (very weak and not easy to detect) 2. N-H deformation vibration, in-plane: NH in-plane deformation, 1650-1550 cm-1 (very weak and difficult to detect) 3. N-H deformation vibration, out-of-plane: NH out-of-plane deformation, 900-650 cm-1 (broad, medium strong) 4. C-N stretching vibration: C-N stretching,1220-1020 cm-1 5. C-H stretching vibration-CH2-NH-CH2- or -CH2-NH-CH3: C-H stretching, ca 2800 cm-1

Aromatic Secondary Amines, N atom attached to C atom of side chain Absorption features are the same as those listed for secondary amines, but overlay the absorption features of the aromatic ring.

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Aromatic Secondary Amines, N atom attached to C atom of aromatic ring 1. N-H stretching vibration: N-H stretching, near 3400 cm-1 (stronger than that of aliphatic secondary amines) 2. N-H deformation vibration, in-plane: N-H in-plane deformation, ca 1600 cm-1 (in many instances, very strong and characteristic of N atom attached to C atom of aromatic ring) 3. N-H deformation vibration, out-of-plane: N-H out-of-plane deformation, 900- 600 cm-1 (usually masked by absorption features of aromatic ring) 4. C-N stretching vibration: Aryl C-N stretching, 1350-1280 cm-1 5. C-N stretching vibration: Alkyl C-N stretching, 1280-1230 cm-1 6. C-H stretching vibration of –N-CH3 │ C-H stretching, ca 2800 cm-1

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Secondary Aromatic Amines Aliphatic Amines 1. N-H stretching vibration: NH stretching, near 3300 cm-1 (very weak and not easy to detect) 2. N-H deformation vibration, in-plane: NH in-plane deformation, 1650-1550 cm-1 (very weak and difficult to detect) 3. N-H deformation vibration, out-of-plane: NH out-of-plane deformation, 900-650 cm-1 (broad, medium strong) 4. C-N stretching vibration: C-N stretching,1220-1020 cm-1 5. C-H stretching vibration-CH2-NH-CH2- or -CH2-NH-CH3: C-H stretching, ca 2800 cm-1

Aromatic Secondary Amines, N atom attached to C atom of side chain Absorption features are the same as those listed for secondary amines, but overlay the absorption features of the aromatic ring.

Aromatic Secondary Amines, N atom attached to C atom of aromatic ring

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

1. N-H stretching vibration: N-H stretching, near 3400 cm-1 (stronger than that of aliphatic secondary amines) 2. N-H deformation vibration, in-plane: N-H in-plane deformation, ca 1600 cm-1 (in many instances, very strong and characteristic of N atom attached to C atom of aromatic ring) 3. N-H deformation vibration, out-of-plane: N-H out-of-plane deformation, 900- 600 cm-1 (usually masked by absorption features of aromatic ring) 4. C-N stretching vibration: Aryl C-N stretching, 1350-1280 cm-1 5. C-N stretching vibration: Alkyl C-N stretching, 1280-1230 cm-1 6. C-H stretching vibration of –N-CH3 │ C-H stretching, ca 2800 cm-1

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Tertiary Amines Aliphatic Tertiary Amines 1. C-H stretching vibration of (-CH2)3N, (-CH2)2N-CH3, and -CH2N (CH3)2 C-H stretching, ca 2800 cm-1 2. C-N stretching vibration: C-N stretching, 1230-1150 cm-1 3. C-N stretching vibration: C-N stretching, 1130-1030 cm-1

Aromatic Tertiary Amines, N atom attached to C atom of side chain 1. C-H stretching vibration of-N-CH2- and -N(CH3)2 │ CH3 C-H stretching, ca 2800 cm-1 2. C-N stretching vibration: Aryl C-N stretching, 1360-1310 cm-1 3. C-N stretching vibration: Alkyl C-N stretching, 1280-1180 cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

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Tertiary Amines Aliphatic Tertiary Amines 1. C-H stretching vibration of (-CH2)3N, (-CH2)2N-CH3, and -CH2N (CH3)2 C-H stretching, ca 2800 cm-1 2. C-N stretching vibration: C-N stretching, 1230-1150 cm-1 3. C-N stretching vibration: C-N stretching, 1130-1030 cm-1

Aromatic Tertiary Amines. N atom attached to C atom of side chain 1. C-H stretching vibration of-N-CH2- and -N(CH3)2 │ CH3 C-H stretching, ca 2800 cm-1 2. C-N stretching vibration: Aryl C-N stretching, 1360-1310 cm-1 3. C-N stretching vibration: Alkyl C-N stretching, 1280-1180 cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

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Pyridines 1. C=C and C=N stretching vibration: C=C and C=N stretching, 1660-1590 cm-1 (usually a doublet) near 1500 cm-1 2. C-H deformation vibration of adjacent ring H’s: ring CH deformation, unsubstituted 746 cm-1 2-monosubstituted, 780-740 cm-1 3-monosubstituted, 810-789 cm-1 4-monosubstituted, 820-794 cm-1 2,3-disubstituted, 800-787 cm-1 2,4-disubstituted, 813 cm-1 2,5-disubstituted, 826-813 cm-1 2,6-disubstituted, 813-769 cm-1 2,4,6-trisubstituted, 833-813 cm-1 3. Ring deformation vibration: ring deformation, unsubstituted, 700 cm-1 2-monosubstituted, 730 cm-1 3-monosubstituted, 712 cm-1 4-monosubstituted, 775-709 cm-1 2,3-disubstituted, 741-725 cm-1 2,4-disubstituted, 758 cm-1 2,5-disubstituted, 735-725 cm-1 2,6-disubstituted, 752-725 cm-1 2,4,6-trisubstituted, ------------4. C-H stretching vibration: C-H stretching, near 3020 cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

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Pyridines and Quinolines 1. C=C and C=N stretching vibration: C=C and C=N stretching, 1660-1590 cm-1 (usually a doublet) near 1500 cm-1 2. C-H deformation vibration of adjacent ring H’s: ring CH deformation, unsubstituted 746 cm-1 2-monosubstituted, 780-740 cm-1 3-monosubstituted, 810-789 cm-1 4-monosubstituted, 820-794 cm-1 2,3-disubstituted, 800-787 cm-1 2,4-disubstituted, 813 cm-1 2,5-disubstituted, 826-813 cm-1 2,6-disubstituted, 813-769 cm-1 2,4,6-trisubstituted, 833-813 cm-1 3. Ring deformation vibration: ring deformation, unsubstituted, 700 cm-1 2-monosubstituted, 730 cm-1 3-monosubstituted, 712 cm-1 4-monosubstituted, 775-709 cm-1 2,3-disubstituted, 741-725 cm-1 2,4-disubstituted, 758 cm-1 2,5-disubstituted, 735-725 cm-1 2,6-disubstituted, 752-725 cm-1 2,4,6-trisubstituted, ------------4. C-H stretching vibration: C-H stretching, near 3020 cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

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Miscellaneous Nitrogen Heteroaromatics 1. 2. 3. 4.

C=C and C=N stretching vibrations C-H deformation vibration of adjacent ring H’s Ring deformation vibration C-H stretching vibration

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Hydrazines Similar to those of corresponding amines 1. N-H stretching vibrations: N-H stretching, near 3300 cm-1 2. N-H deformation vibrations: N-H in-plane deformation, near 1600 cm-1 N-H out-of-plane deformation, near 800 cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

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Amine Salts Primary Amine Salts 1. NH3+ stretching vibration: NH3+ asymmetric, symmetric stretching, 3200-2800 cm-1 (strong, broad absorption) 2. NH3+ deformation NH3+ asymmetric deformation, 1625-1560 cm-1 NH3+ symmetric deformation, 1550-1505 cm-1 3. Combination bands of NH3+ deformation vibration: NH3+ combination bands, 2800 - 2400 cm-1 (sharp, weak absorption)

Secondary Amine Salts 1. NH2+ stretching vibration: NH2+ asymmetric, symmetric stretching, 3000-2700 cm-1 (sharp, weak absorption) 2. NH2+ deformation vibration: NH2+ deformation, 1620-1560 cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

3. Combination bands of NH2+ deformation vibration: NH2+ combination bands, 2700 - 2300 cm-1

Tertiary Amine Salts 1. NH+ stretching vibration: NH+ stretching, 2700 - 2330 cm-1 (several bands)

Quaternary Amine Salts No characteristic absorption bands.

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Oximes Oximes 1. C=N stretching vibration: C=N stretching, 1690-1620 cm-1 (weak to medium strong absorption) 2. O-H stretching vibration (H-bonded): O-H stretching, 3300-3150 cm-1 (broad, strong absorption) 3. N-O stretching vibration: N-O stretching, near 930 cm-1

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Hydrazones Oximes 1. C=N stretching vibration: C=N stretching, 1690-1620 cm-1 (weak to medium strong absorption) 2. O-H stretching vibration (H-bonded): O-H stretching, 3300-3150 cm-1 (broad, strong absorption) 3. N-O stretching vibration: N-O stretching, near 930 cm-1

Hydrazones (-CH=N-N) 1. C=N stretching vibration: C=N stretching, 1670-1600 cm-1 (medium to strong absorption)

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Azines Oximes 1. C=N stretching vibration: C=N stretching, 1690-1620 cm-1 (weak to medium strong absorption) 2. O-H stretching vibration (H-bonded): O-H stretching, 3300-3150 cm-1 (broad, strong absorption) 3. N-O stretching vibration: N-O stretching, near 930 cm-1

Azines (-CH=N-N=CH-) 1. C=N stretching vibration: C=N stretching, 1670-1600 cm-1 (medium to strong absorption)

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Amidines Oximes 1. C=N stretching vibration: C=N stretching, 1690-1620 cm-1 (weak to medium strong absorption) 2. O-H stretching vibration (H-bonded): O-H stretching, 3300-3150 cm-1 (broad, strong absorption) 3. N-O stretching vibration: N-O stretching, near 930 cm-1

Amidines (-NH-C=N-) 1. C=N stretching vibration: C=N stretching, 1670-1600 cm-1 (medium to strong absorption)

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Hydroxamic Acids Oximes 1. C=N stretching vibration: C=N stretching, 1690-1620 cm-1 (weak to medium strong absorption) 2. O-H stretching vibration (H-bonded): O-H stretching, 3300-3150 cm-1 (broad, strong absorption) 3. N-O stretching vibration: N-O stretching, near 930 cm-1

Hydroxamic Acids 1. C=N stretching vibration: C=N stretching, 1670-1600 cm-1 (medium to strong absorption)

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AZO Compounds The absorption arising from the N=N stretching vibration of aromatic azo compounds is weak and occurs at the same region as the absorption arising from aromatic ring vibrations and the absorption arising from the deformation vibration of akyl substituents. Because of coupling or overlapping of such absorption bands, the detection of absorption due, specifically, to N=N linkage is difficult and questionable. Other methods of examina-tion such as Raman -1 spectroscopy (region of 1550- 1400 cm ) afford more precise information concerning the presence of this linkage.

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Triazenes AZO Compounds The absorption arising from the N=N stretching vibration of aromatic azo compounds is weak and occurs at the same region as the absorption arising from aromatic ring vibrations and the absorption arising from the deformation vibration of akyl substituents. Because of coupling or overlapping of such absorption bands, the detection of absorption due, specifically, to N=N linkage is difficult and questionable. Other methods of examination such as Raman spectroscopy (region of 1550- 1400 cm-1) afford more precise information concerning the presence of this linkage.

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Cumulative Double Bonds- Isocyanates Isocyanates 1. N=C=O stretching vibration: N=C=O stretching, 2275-2265 cm-1 (very strong absorption)

Carbodiimides 1. N=C=N stretching vibration: N=C=N stretching, 2170-2100 cm-1 (very strong, sharp)

Isothiocyanates 1. N=C=S stretching vibration: N=C=S stretching, 2150-2020 cm-1 (very strong, usually split or with shoulders)

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Cumulative Double Bonds - Carbodiimides Isocyanates 1. N=C=O stretching vibration: N=C=O stretching, 2275-2265 cm-1 (very strong absorption)

Carbodiimides 1. N=C=N stretching vibration: N=C=N stretching, 2170-2100 cm-1 (very strong, sharp)

Isothiocyanates 1. N=C=S stretching vibration: N=C=S stretching, 2150-2020 cm-1 (very strong, usually split or with shoulders)

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Cumulative Double Bonds - Isothiocyanates Isocyanates 1. N=C=O stretching vibration: N=C=O stretching, 2275-2265 cm-1 (very strong absorption)

Carbodiimides 1. N=C=N stretching vibration: N=C=N stretching, 2170-2100 cm-1 (very strong, sharp)

Isothiocyanates 1. N=C=S stretching vibration: N=C=S stretching, 2150-2020 cm-1 (very strong, usually split or with shoulders)

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Nitriles 1. C≡N stretching vibration: C≡N stretching, (saturated aliphatic nitriles), 2260-2240 cm-1 (weak to strong, sharp) Conjugation of C≡N with olefinic C=C and aromatic ring C=C slightly lowers the frequency and band location of the C≡N stretching vibration. This effect is accompanied by an increase in the intensity of the C≡N absorption band.

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Nitriles 1. C≡N stretching vibration: C≡N stretching, (saturated aliphatic nitriles), 2260-2240 cm-1 (weak to strong, sharp) Conjugation of C≡N with olefinic C=C and aromatic ring C=C slightly lowers the frequency and band location of the C≡N stretching vibration. This effect is accompanied by an increase in the intensity of the C≡N absorption band.

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Nitriles 1. C≡N stretching vibration: C≡N stretching, (saturated aliphatic nitriles), 2260-2240 cm-1 (weak to strong, sharp) Conjugation of C≡N with olefinic C=C and aromatic ring C=C slightly lowers the frequency and band location of the C≡N stretching vibration. This effect is accompanied by an increase in the intensity of the C≡N absorption band.

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Cyanamides Cyanamides 1. C≡N stretching vibration: C≡N stretching, 2225-2210 cm-1 (sharp, very strong absorption)

Isocyanides 1. -N≡C stretching vibration: -N≡C stretching, 2160-2110 cm-1 (sharp, strong absorption)

Thiocyanates (-S-C≡N) 1. –S-C≡N stretching vibration: -S-C≡N stretching, 2160-2140 cm-1 (sharp, very strong absorption)

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Thiocyanates Cyanamides 1. C≡N stretching vibration: C≡N stretching, 2225-2210 cm-1 (sharp, very strong absorption)

Isocyanides 1. -N≡C stretching vibration: -N≡C stretching, 2160-2110 cm-1 (sharp, strong absorption)

Thiocyanates (-S-C≡N) 1. –S-C≡N stretching vibration: -S-C≡N stretching, 2160-2140 cm-1 (sharp, very strong absorption)

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Nitroso, N-Nitroso and Nitrite Compounds 1. N=O stretching vibration: C-N=O N=O stretching (aliphatic monomer), 1621-1539 cm-1 N=O stretching (aromatic monomer), 1513-1488 cm-1 N=O stretching (aliphatic dimer) trans, 1290-1176 cm-1 cis, 1420 -1330 and 1344 -1323 cm-1 N=O stretching (aromatic dimer) trans,1299 -1253 cm-1 cis ,1409 and 1397 -1389 cm-1 N-N=O N=O stretching, near 1448 cm-1 (strong, slightly broadened) 2. C-N or N-N stretching vibration: C-N stretching, near 1100 cm-1 N-N stretching, 1065-1015 cm-1

Nitrites (-O-N=O) 1. N=O stretching vibration: N=O stretching, 1650-1620 cm-1 2. C-N stretching vibration: C-N stretching, 815-770 cm-1

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Nitroso, N-Nitroso and Nitrite Compounds 1. N=O stretching vibration: C-N=O N=O stretching (aliphatic monomer), 1621-1539 cm-1 N=O stretching (aromatic monomer), 1513-1488 cm-1 N=O stretching (aliphatic dimer) trans, 1290-1176 cm-1 cis, 1420 -1330 and 1344 -1323 cm-1 N=O stretching (aromatic dimer) trans,1299 -1253 cm-1 cis ,1409 and 1397 -1389 cm-1 N-N=O N=O stretching, near 1448 cm-1 (strong, slightly broadened) 2. C-N or N-N stretching vibration: C-N stretching, near 1100 cm-1 N-N stretching, 1065-1015 cm-1

Nitrites (-O-N=O) 1. N=O stretching vibration: N=O stretching, 1650-1620 cm-1 2. C-N stretching vibration: C-N stretching, 815-770 cm-1

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Nitroso, N-Nitroso and Nitrite Compounds 1. N=O stretching vibration: C-N=O N=O stretching (aliphatic monomer), 1621-1539 cm-1 N=O stretching (aromatic monomer), 1513-1488 cm-1 N=O stretching (aliphatic dimer) trans, 1290-1176 cm-1 cis, 1420 -1330 and 1344 -1323 cm-1 N=O stretching (aromatic dimer) trans,1299 -1253 cm-1 cis ,1409 and 1397 -1389 cm-1 N-N=O N=O stretching, near 1448 cm1

(strong, slightly broadened) 2. C-N or N-N stretching vibration: C-N stretching, near 1100 cm-1 N-N stretching, 1065-1015 cm-1

Nitrites (-O-N=O) 1. N=O stretching vibration: N=O stretching, 1650-1620 cm-1 2. C-N stretching vibration: C-N stretching, 815-770 cm-1

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Nitro Compounds Aliphatic 1. C-NO2 asymmetric stretching vibration: NO2 asymmetric stretching, 1590-1530 cm-1 (strong) 2. C-NO2 symmetric stretching vibration: NO2 symmetric stretching, 1390-1350 cm-1 (weaker than asymmetric stretching)

Aromatic 3. Ar-NO2 asymmetric stretching vibrations: NO2 asymmetric stretching, 1530-1510 cm-1 (strong) 4. Ar-NO2 symmetric stretching vibration: NO2 symmetric stretching, 1350-1330 cm-1

N-Nitro Compounds 1. NO2 symmetric and asymmetric (similar to aliphatic nitro compounds with addition of a third strong band at 1240 cm-1)

Nitrate Compounds

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1. O-NO2 asymmetric stretching vibration: NO2 asymmetric stretching, 1640-1610 cm-1 2. O-NO2 symmetric stretching vibration: NO2 symmetric stretching, 1290-1280 cm-1

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Nitro Compounds Aliphatic 1. C-NO2 asymmetric stretching vibration: NO2 asymmetric stretching, 1590-1530 cm-1 (strong) 2. C-NO2 symmetric stretching vibration: NO2 symmetric stretching, 1390-1350 cm-1 (weaker than asymmetric stretching)

Aromatic 3. Ar-NO2 asymmetric stretching vibrations: NO2 asymmetric stretching, 1530-1510 cm-1 (strong) 4. Ar-NO2 symmetric stretching vibration: NO2 symmetric stretching, 1350-1330 cm-1

N-Nitro Compounds 1. NO2 symmetric and asymmetric (similar to aliphatic nitro compounds with addition of a third strong band at 1240 cm-1)

Nitrate Compounds

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1. O-NO2 asymmetric stretching vibration: NO2 asymmetric stretching, 1640-1610 cm-1 2. O-NO2 symmetric stretching vibration: NO2 symmetric stretching, 1290-1280 cm-1

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N-Nitro Compounds Aliphatic - Nitro 1. C-NO2 asymmetric stretching vibration: NO2 asymmetric stretching, 1590-1530 cm-1 (strong) 2. C-NO2 symmetric stretching vibration: NO2 symmetric stretching, 1390-1350 cm-1 (weaker than asymmetric stretching)

Aromatic - Nitro 3. Ar-NO2 asymmetric stretching vibrations: NO2 asymmetric stretching, 1530-1510 cm-1 (strong) 4. Ar-NO2 symmetric stretching vibration: NO2 symmetric stretching, 1350-1330 cm-1

N-Nitro Compounds 1. NO2 symmetric and asymmetric (similar to aliphatic nitro compounds with addition of a third strong band at 1240 cm-1)

Nitrate Compounds 1. O-NO2 asymmetric stretching vibration: NO2 asymmetric stretching, 1640-1610 cm-1 2. O-NO2 symmetric stretching vibration: NO2 symmetric stretching, 1290-1280 cm-1

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Silicon Compounds 1. Si-H stretching vibration: Si-H stretching, 2160-2120 cm-1 (strong, sharp) 2. Si-CH3 asymmetric deformation vibration: Si-CH3 asymmetric deformation, 1420-1390 cm-1 (medium intensity) 3. Si-CH3 symmetric deformation vibration: Si-CH3 symmetric deformation, 1260-1230 cm-1 (strong, sharp) 4. Ar-Si aromatic silanes contain two sharp, strong bands of uncertain origin: 1430-1410 cm-1 and 1120-1100 cm-1 5. Si-C stretching vibration: Si-C stretching, 900-700 cm-1 (strong, broad)

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Phosphorus Compounds 1. P-CH2 deformation vibration: C-H deformation, 1440-1400 cm-1 (medium intensity, sharp absorption) 2. P=O stretching vibration: P=O stretching, 1310-1240 cm-1 (sharp, strong absorption) 3. P+ -Ar, near 1110 cm-1 (strong, sharp absorption) 4. P+ -Ar, near 990 cm-1 (medium intensity, sharp absorption) The spectra of other phosphorus containing functional groups may be found as follows: P-O-C, see Ethers (O=P)-O-C, see Esters

Coming Soon! P-OH, see Alcohols (O=P)-OH, see Acids

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Sulfides 1. CH2-S-C deformation vibration: CH2-S-C deformation, 1440-1415 cm-1 (medium intensity, sharp band) 2. CH2-S- wagging vibration: CH2-S wagging, 1270-1220 cm-1 (medium to strong absorption) 3. C-S stretching vibration: C-S stretching, 700-600 cm-1 (weak absorption band) 4. CH3-S asymmetric deformation vibration: CH2-S- asymmetric deformation,1440-1415 cm-1 (medium intensity, sharp absorption) 5. Ar-S1090 cm-1 (medium intensity, sharp absorption) 6. S-S stretching vibration: S-S stretching, 500-400 cm-1 (very weak)

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Sulfides 1. CH2-S-C deformation vibration: CH2-S-C deformation, 1440-1415 cm-1 (medium intensity, sharp band) 2. CH2-S- wagging vibration: CH2-S wagging, 1270-1220 cm-1 (medium to strong absorption) 3. C-S stretching vibration: C-S stretching, 700-600 cm-1 (weak absorption band) 4. CH3-S asymmetric deformation vibration: CH2-S- asymmetric deformation,1440-1415 cm-1 (medium intensity, sharp absorption) 5. Ar-S1090 cm-1 (medium intensity, sharp absorption) 6. S-S stretching vibration: S-S stretching, 500-400 cm-1 (very weak)

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Sulfides 1. CH2-S-C deformation vibration: CH2-S-C deformation, 1440-1415 cm-1 (medium intensity, sharp band) 2. CH2-S- wagging vibration: CH2-S wagging, 1270-1220 cm-1 (medium to strong absorption) 3. C-S stretching vibration: C-S stretching, 700-600 cm-1 (weak absorption band) 4. CH3-S asymmetric deformation vibration: CH2-S- asymmetric deformation,1440-1415 cm-1 (medium intensity, sharp absorption) 5. Ar-S1090 cm-1 (medium intensity, sharp absorption) 6. S-S stretching vibration: S-S stretching, 500-400 cm-1 (very weak)

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Disulfides 1. CH2-S-C deformation vibration: CH2-S-C deformation, 1440-1415 cm-1 (medium intensity, sharp band) 2. CH2-S- wagging vibration: CH2-S wagging, 1270-1220 cm-1 (medium to strong absorption) 3. C-S stretching vibration: C-S stretching, 700-600 cm-1 (weak absorption band) 4. CH3-S asymmetric deformation vibration: CH2-S- asymmetric deformation,1440-1415 cm-1 (medium intensity, sharp absorption) 5. Ar-S1090 cm-1 (medium intensity, sharp absorption) 6. S-S stretching vibration: S-S stretching, 500-400 cm-1 (very weak)

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Thiols 1. S-H stretching vibration: S-H stretching, 2600-2550 cm-1 (weak, broadened absorption band) 2. CH2-S-C deformation vibration: CH2-S-C deformation, 1440-1415 cm-1 (medium intensity, sharp absorption) 3. CH2-S wagging vibration: CH2-S wagging, 1270-1220 cm-1 (medium to strong intensity) 4. C-S stretching vibration: C-S stretching, 700-600 cm-1 (weak intensity)

Coming Soon! 5. Ar-S,1100-1080 cm-1 (medium intensity, sharp absorption) Location and appearance of bands similar to sulfides, except with the addition of the –S-H stretching vibration near 2575 cm-1.

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Thiols 1. S-H stretching vibration: S-H stretching, 2600-2550 cm-1 (weak, broadened absorption band) 2. CH2-S-C deformation vibration: CH2-S-C deformation, 1440-1415 cm-1 (medium intensity, sharp absorption) 3. CH2-S wagging vibration: CH2-S wagging, 1270-1220 cm-1 (medium to strong intensity) 4. C-S stretching vibration: C-S stretching, 700-600 cm-1 (weak intensity)

Coming Soon! 5. Ar-S,1100-1080 cm-1 (medium intensity, sharp absorption)

Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Location and appearance of bands similar to sulfides, except with the addition of the –S-H stretching vibration near 2575 cm-1.

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Sulfoxides Sulfoxides 1. S=O stretching vibration: S=O stretching, 1060-1020 cm-1 (strong absorption)

Sulfones 1. SO2 asymmetric stretching vibration: SO2 asymmetric stretching, 1350-1300 cm-1 (strong, may be split) 2. SO2 symmetric stretching vibration: SO2 symmetric stretching, 1160 -1130 cm-1 (strong intensity, slightly broadened)

Sulfonyl Halides 1. F- SO2 asymmetric stretching vibration: SO2 asymmetric stretching, 1410-1390 cm-1 2. F- SO2 symmetric stretching vibration: SO2 symmetric stretching, 1220-1200 cm-1 3. F- SO2 stretching vibration: F-S stretching, 800 cm-1 (strong, broadened absorption band) 4. Cl- SO2 asymmetric stretching vibration:

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SO2 asymmetric stretching, near 1335 cm-1 5. Cl -SO2 symmetric stretching vibration: SO2 symmetric stretching, near 1175 cm-1

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Sulfones Sulfoxides 1. S=O stretching vibration: S=O stretching, 1060-1020 cm-1 (strong absorption)

Sulfones 1. SO2 asymmetric stretching vibration: SO2 asymmetric stretching, 1350-1300 cm-1 (strong, may be split) 2. SO2 symmetric stretching vibration: SO2 symmetric stretching, 1160 -1130 cm-1 (strong intensity, slightly broadened)

Sulfonyl Halides 1. F- SO2 asymmetric stretching vibration: SO2 asymmetric stretching, 1410-1390 cm-1 2. F- SO2 symmetric stretching vibration:

Coming Soon!

SO2 symmetric stretching, 1220-1200 cm-1 3. F- SO2 stretching vibration:

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F-S stretching, 800 cm-1 (strong, broadened absorption band) 4. Cl- SO2 asymmetric stretching vibration: SO2 asymmetric stretching, near 1335 cm-1 5. Cl -SO2 symmetric stretching vibration: SO2 symmetric stretching, near 1175 cm-1

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Sulfonyl Halides Sulfoxides 1. S=O stretching vibration: S=O stretching, 1060-1020 cm-1 (strong absorption)

Sulfones 1. SO2 asymmetric stretching vibration: SO2 asymmetric stretching, 1350-1300 cm-1 (strong, may be split) 2. SO2 symmetric stretching vibration: SO2 symmetric stretching, 1160 -1130 cm-1 (strong intensity, slightly broadened)

Sulfonyl Halides 1. F- SO2 asymmetric stretching vibration: SO2 asymmetric stretching, 1410-1390 cm-1 2. F- SO2 symmetric stretching vibration:

Coming Soon!

SO2 symmetric stretching, 1220-1200 cm-1 3. F- SO2 stretching vibration:

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F-S stretching, 800 cm-1 (strong, broadened absorption band) 4. Cl- SO2 asymmetric stretching vibration: SO2 asymmetric stretching, near 1335 cm-1 5. Cl -SO2 symmetric stretching vibration: SO2 symmetric stretching, near 1175 cm-1

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Sulfonic Acids Acids 1. HO-SO2- asymmetric stretching vibration: S=O asymmetric stretching, 1250-1150 cm-1 (intense and broadened) 2. HO-SO2- symmetric stretching vibration: S=O symmetric stretching, 1100-1000 cm-1 (medium to strong intensity, sharp)

Salts Similar band ranges for free sulfonic acids. 1. HO-SO2- asymmetric stretching vibration: S=O asymmetric stretching, 1250-1150 cm-1 (intense and broadened) 2. HO-SO2- symmetric stretching vibration: S=O symmetric stretching, 1100-1000 cm-1 (medium to strong intensity, sharp)

Sulfates

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1. O-SO2-O asymmetric stretching vibration: S=O asymmetric stretching, 1440-1350 cm-1 (strong) 2. O-SO2-O symmetric stretching vibration: S=O symmetric stretching,1230-1150 cm-1 (strong) 3. C-O-SO2 stretching viibration: C-O-S stretching, 810-770 cm-1 (strong intensity, broad)

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Sulfonic Acid Salts Acids 1. HO-SO2- asymmetric stretching vibration: S=O asymmetric stretching, 1250-1150 cm-1 (intense and broadened) 2. HO-SO2- symmetric stretching vibration: S=O symmetric stretching, 1100-1000 cm-1 (medium to strong intensity, sharp)

Salts Similar band ranges for free sulfonic acids. 1. HO-SO2- asymmetric stretching vibration: S=O asymmetric stretching, 1250-1150 cm-1 (intense and broadened) 2. HO-SO2- symmetric stretching vibration: S=O symmetric stretching, 1100-1000 cm-1 (medium to strong intensity, sharp)

Sulfates

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1. O-SO2-O asymmetric stretching vibration: S=O asymmetric stretching, 1440-1350 cm-1 (strong) 2. O-SO2-O symmetric stretching vibration: S=O symmetric stretching,1230-1150 cm-1 (strong) 3. C-O-SO2 stretching viibration: C-O-S stretching, 810-770 cm-1 (strong intensity, broad)

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Sulfonic Acid Esters Acids 1. HO-SO2- asymmetric stretching vibration: S=O asymmetric stretching, 1250-1150 cm-1 (intense and broadened) 2. HO-SO2- symmetric stretching vibration: S=O symmetric stretching, 1100-1000 cm-1 (medium to strong intensity, sharp)

Salts Similar band ranges for free sulfonic acids. 1. HO-SO2- asymmetric stretching vibration: S=O asymmetric stretching, 1250-1150 cm-1 (intense and broadened) 2. HO-SO2- symmetric stretching vibration: S=O symmetric stretching, 1100-1000 cm-1 (medium to strong intensity, sharp)

Sulfates

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1. O-SO2-O asymmetric stretching vibration: S=O asymmetric stretching, 1440-1350 cm-1 (strong) 2. O-SO2-O symmetric stretching vibration: S=O symmetric stretching,1230-1150 cm-1 (strong) 3. C-O-SO2 stretching viibration: C-O-S stretching, 810-770 cm-1 (strong intensity, broad)

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Sulfuric Acid Esters Acids 1. HO-SO2- asymmetric stretching vibration: S=O asymmetric stretching, 1250-1150 cm-1 (intense and broadened) 2. HO-SO2- symmetric stretching vibration: S=O symmetric stretching, 1100-1000 cm-1 (medium to strong intensity, sharp)

Salts Similar band ranges noted above for free sulfonic acids. 1. HO-SO2- asymmetric stretching vibration: S=O asymmetric stretching, 1250-1150 cm-1 (intense and broadened) 2. HO-SO2- symmetric stretching vibration: S=O symmetric stretching, 1100-1000 cm-1 (medium to strong intensity, sharp)

Sulfates

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1. O-SO2-O asymmetric stretching vibration: S=O asymmetric stretching, 1440-1350 cm-1 (strong) 2. O-SO2-O symmetric stretching vibration: S=O symmetric stretching,1230-1150 cm-1 (strong) 3. C-O-SO2 stretching viibration: C-O-S stretching, 810-770 cm-1 (strong intensity, broad)

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Thioamides 1. NH and NH2 stretching vibrations: NH stretching and NH2 stretching, 3360-3100 cm-1 2. NH deformation and C-N stretching combination band: NH deformation and C-N stretching,1650-1520 cm-1

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Thioureas 1. NH and NH2 stretching vibrations: NH stretching and NH2 stretching, 3360-3100 cm-1 2. NH deformation and C-N stretching combination band: NH deformation and C-N stretching,1650-1520 cm-1

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Sulfonamides S=O stretching vibrations: 1. S=O asymmetric stretching, 1350-1310 cm-1 (strong intensity) 2. S=O symmetric stretching, 1180-1140 cm-1 (strong intensity) In solution, these bands appear at slightly higher wavenumber regions.

Primary Sulfonamides 1. N-H stretching vibrations: NH2 asymmetric stretching, 3390-3330 cm-1 NH2 symmetric stretching, 3300-3245 cm-1

Secondary Sulfonamides 1. N-H stretching vibration: NH stretching, 3280-3250 cm-1

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Sulfamides S=O stretching vibrations: 1. S=O asymmetric stretching, 1350-1310 cm-1 (strong intensity) 2. S=O symmetric stretching, 1180-1140 cm-1 (strong intensity) In solution, these bands appear at slightly higher wavenumber regions.

Primary Sulfonamides 1. N-H stretching vibrations: NH2 asymmetric stretching, 3390-3330 cm-1 NH2 symmetric stretching, 3300-3245 cm-1

Secondary Sulfonamides 1. N-H stretching vibration: NH stretching, 3280-3250 cm-1

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Ethers Acetals, Furans, Peroxides, Silicon Ethers, Phosphorus Ethers Aliphatic Ethers 1. C-O-C stretching vibration: -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of side chain. 1. C-O-C stretching vibration: -C-O-C stretching, same as for aliphatic ethers -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of aromatic ring. 1. C-O-C stretching vibration: =C-O-C stretching, 1270-1230 cm-1 (strong absorption band) 1050-1010 cm-1 (medium strong absorption band)

Heterocyclic systems Three membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1250 cm-1 (strong absorption band) near 830 cm-1 (medium strong absorption band)

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Four membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1030 cm-1 (strong absorption band) -C-O-C- asymmetric stretching, near 980 cm-1 (strong absorption band)

Five membered rings 1. C-O-C stretching vibration: -C-O-C- asymmetric stretching, near 1050 cm-1 (strong absorption band) -C-O-C- symmetric stretching, near 900 cm-1 (strong absorption band)

Larger rings 1. C-O-C stretching vibration: -C-O-C- stretching, near 1100 cm-1 (strong absorption band) In most instances, when used alone, strong absorption at the cited regions is considered to be related to the stretching vibration of only a C-O- link. Another absorption feature of the spectrum should be taken into consideration when using the C-O- absorption band as indicative of an ether group. For example, the absence of characteristic absorption features of those functional groups which contain the C-O- link (alcohol groups, ester groups, etc.) increases the probability of the C-Oabsorption as indicative of an ether group.

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Ethers Acetals, Furans, Peroxides, Silicon Ethers, Phosphorus Ethers Aliphatic Ethers 1. C-O-C stretching vibration: -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of side chain. 1. C-O-C stretching vibration: -C-O-C stretching, same as for aliphatic ethers -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of aromatic ring. 1. C-O-C stretching vibration: =C-O-C stretching, 1270-1230 cm-1 (strong absorption band) 1050-1010 cm-1 (medium strong absorption band)

Heterocyclic systems Three membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1250 cm-1 (strong absorption band) near 830 cm-1 (medium strong absorption band)

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Four membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1030 cm-1 (strong absorption band) -C-O-C- asymmetric stretching, near 980 cm-1 (strong absorption band)

Five membered rings 1. C-O-C stretching vibration: -C-O-C- asymmetric stretching, near 1050 cm-1 (strong absorption band) -C-O-C- symmetric stretching, near 900 cm-1 (strong absorption band)

Larger rings 1. C-O-C stretching vibration: -C-O-C- stretching, near 1100 cm-1 (strong absorption band) In most instances, when used alone, strong absorption at the cited regions is considered to be related to the stretching vibration of only a C-O- link. Another absorption feature of the spectrum should be taken into consideration when using the C-O- absorption band as indicative of an ether group. For example, the absence of characteristic absorption features of those functional groups which contain the C-O- link (alcohol groups, ester groups, etc.) increases the probability of the C-Oabsorption as indicative of an ether group.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

Go to: home • ir • proton nmr • carbon nmr • mass spec

Ethers Acetals, Furans, Peroxides, Silicon Ethers, Phosphorus Ethers Aliphatic Ethers 1. C-O-C stretching vibration: -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of side chain. 1. C-O-C stretching vibration: -C-O-C stretching, same as for aliphatic ethers -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of aromatic ring. 1. C-O-C stretching vibration: =C-O-C stretching, 1270-1230 cm-1 (strong absorption band) 1050-1010 cm-1 (medium strong absorption band)

Heterocyclic systems Three membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1250 cm-1 (strong absorption band) near 830 cm-1 (medium strong absorption band)

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Four membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1030 cm-1 (strong absorption band) -C-O-C- asymmetric stretching, near 980 cm-1 (strong absorption band)

Five membered rings 1. C-O-C stretching vibration: -C-O-C- asymmetric stretching, near 1050 cm-1 (strong absorption band) -C-O-C- symmetric stretching, near 900 cm-1 (strong absorption band)

Larger rings 1. C-O-C stretching vibration: -C-O-C- stretching, near 1100 cm-1 (strong absorption band) In most instances, when used alone, strong absorption at the cited regions is considered to be related to the stretching vibration of only a C-O- link. Another absorption feature of the spectrum should be taken into consideration when using the C-O- absorption band as indicative of an ether group. For example, the absence of characteristic absorption features of those functional groups which contain the C-O- link (alcohol groups, ester groups, etc.) increases the probability of the C-Oabsorption as indicative of an ether group.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

Go to: home • ir • proton nmr • carbon nmr • mass spec

Ethers Acetals, Furans, Peroxides, Silicon Ethers, Phosphorus Ethers Aliphatic Ethers 1. C-O-C stretching vibration: -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of side chain. 1. C-O-C stretching vibration: -C-O-C stretching, same as for aliphatic ethers -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of aromatic ring. 1. C-O-C stretching vibration: =C-O-C stretching, 1270-1230 cm-1 (strong absorption band) 1050-1010 cm-1 (medium strong absorption band)

Heterocyclic systems Three membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1250 cm-1 (strong absorption band) near 830 cm-1 (medium strong absorption band)

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Four membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1030 cm-1 (strong absorption band) -C-O-C- asymmetric stretching, near 980 cm-1 (strong absorption band)

Five membered rings 1. C-O-C stretching vibration: -C-O-C- asymmetric stretching, near 1050 cm-1 (strong absorption band) -C-O-C- symmetric stretching, near 900 cm-1 (strong absorption band)

Larger rings 1. C-O-C stretching vibration: -C-O-C- stretching, near 1100 cm-1 (strong absorption band) In most instances, when used alone, strong absorption at the cited regions is considered to be related to the stretching vibration of only a C-O- link. Another absorption feature of the spectrum should be taken into consideration when using the C-O- absorption band as indicative of an ether group. For example, the absence of characteristic absorption features of those functional groups which contain the C-O- link (alcohol groups, ester groups, etc.) increases the probability of the C-Oabsorption as indicative of an ether group.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

Go to: home • ir • proton nmr • carbon nmr • mass spec

Ethers Acetals, Furans, Peroxides, Silicon Ethers, Phosphorus Ethers Aliphatic Ethers 1. C-O-C stretching vibration: -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of side chain. 1. C-O-C stretching vibration: -C-O-C stretching, same as for aliphatic ethers -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of aromatic ring. 1. C-O-C stretching vibration: =C-O-C stretching, 1270-1230 cm-1 (strong absorption band) 1050-1010 cm-1 (medium strong absorption band)

Heterocyclic systems Three membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1250 cm-1 (strong absorption band) near 830 cm-1 (medium strong absorption band)

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Four membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1030 cm-1 (strong absorption band) -C-O-C- asymmetric stretching, near 980 cm-1 (strong absorption band)

Five membered rings 1. C-O-C stretching vibration: -C-O-C- asymmetric stretching, near 1050 cm-1 (strong absorption band) -C-O-C- symmetric stretching, near 900 cm-1 (strong absorption band)

Larger rings 1. C-O-C stretching vibration: -C-O-C- stretching, near 1100 cm-1 (strong absorption band) In most instances, when used alone, strong absorption at the cited regions is considered to be related to the stretching vibration of only a C-O- link. Another absorption feature of the spectrum should be taken into consideration when using the C-O- absorption band as indicative of an ether group. For example, the absence of characteristic absorption features of those functional groups which contain the C-O- link (alcohol groups, ester groups, etc.) increases the probability of the C-Oabsorption as indicative of an ether group.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

Go to: home • ir • proton nmr • carbon nmr • mass spec

Ethers Acetals, Furans, Peroxides, Silicon Ethers, Phosphorus Ethers Aliphatic Ethers 1. C-O-C stretching vibration: -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of side chain. 1. C-O-C stretching vibration: -C-O-C stretching, same as for aliphatic ethers -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of aromatic ring. 1. C-O-C stretching vibration: =C-O-C stretching, 1270-1230 cm-1 (strong absorption band) 1050-1010 cm-1 (medium strong absorption band)

Heterocyclic systems Three membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1250 cm-1 (strong absorption band) near 830 cm-1 (medium strong absorption band)

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Four membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1030 cm-1 (strong absorption band) -C-O-C- asymmetric stretching, near 980 cm-1 (strong absorption band)

Five membered rings 1. C-O-C stretching vibration: -C-O-C- asymmetric stretching, near 1050 cm-1 (strong absorption band) -C-O-C- symmetric stretching, near 900 cm-1 (strong absorption band)

Larger rings 1. C-O-C stretching vibration: -C-O-C- stretching, near 1100 cm-1 (strong absorption band) In most instances, when used alone, strong absorption at the cited regions is considered to be related to the stretching vibration of only a C-O- link. Another absorption feature of the spectrum should be taken into consideration when using the C-O- absorption band as indicative of an ether group. For example, the absence of characteristic absorption features of those functional groups which contain the C-O- link (alcohol groups, ester groups, etc.) increases the probability of the C-Oabsorption as indicative of an ether group.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

Go to: home • ir • proton nmr • carbon nmr • mass spec

Ethers Acetals, Furans, Peroxides, Silicon Ethers, Phosphorus Ethers Aliphatic Ethers 1. C-O-C stretching vibration: -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of side chain. 1. C-O-C stretching vibration: -C-O-C stretching, same as for aliphatic ethers -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of aromatic ring. 1. C-O-C stretching vibration: =C-O-C stretching, 1270-1230 cm-1 (strong absorption band) 1050-1010 cm-1 (medium strong absorption band)

Heterocyclic systems Three membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1250 cm-1 (strong absorption band) near 830 cm-1 (medium strong absorption band)

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Four membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1030 cm-1 (strong absorption band) -C-O-C- asymmetric stretching, near 980 cm-1 (strong absorption band)

Five membered rings 1. C-O-C stretching vibration: -C-O-C- asymmetric stretching, near 1050 cm-1 (strong absorption band) -C-O-C- symmetric stretching, near 900 cm-1 (strong absorption band)

Larger rings 1. C-O-C stretching vibration: -C-O-C- stretching, near 1100 cm-1 (strong absorption band) In most instances, when used alone, strong absorption at the cited regions is considered to be related to the stretching vibration of only a C-O- link. Another absorption feature of the spectrum should be taken into consideration when using the C-O- absorption band as indicative of an ether group. For example, the absence of characteristic absorption features of those functional groups which contain the C-O- link (alcohol groups, ester groups, etc.) increases the probability of the C-Oabsorption as indicative of an ether group.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

Go to: home • ir • proton nmr • carbon nmr • mass spec

Ethers Acetals, Furans, Peroxides, Silicon Ethers, Phosphorus Ethers Aliphatic Ethers 1. C-O-C stretching vibration: -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of side chain. 1. C-O-C stretching vibration: -C-O-C stretching, same as for aliphatic ethers -CH2-O-CH2- stretching, 1150-1060 cm-1 (strong absorption band) -CH-O-CH2- stretching, 1170-1070 cm-1 (strong multiple absorption bands) near 1010 cm-1 (strong absorption band) -C-O-CH2- stretching, near 1200 cm-1 (strong absorption band, some splitting) near 1100 cm-1 (1 or 2 strong absorption bands) -CH2=CH-O-CH2- stretching, 1225-1200 cm-1 (strong absorption band) -O-CH2-O- stretching, 1200-1100 cm-1 (strong multiple absorption bands)

Aromatic Ethers, oxygen atom attached to C atom of aromatic ring. 1. C-O-C stretching vibration: =C-O-C stretching, 1270-1230 cm-1 (strong absorption band) 1050-1010 cm-1 (medium strong absorption band)

Heterocyclic systems Three membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1250 cm-1 (strong absorption band) near 830 cm-1 (medium strong absorption band)

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Four membered rings 1. C-O-C stretching vibration: -C-O-C- symmetric stretching, near 1030 cm-1 (strong absorption band) -C-O-C- asymmetric stretching, near 980 cm-1 (strong absorption band)

Five membered rings 1. C-O-C stretching vibration: -C-O-C- asymmetric stretching, near 1050 cm-1 (strong absorption band) -C-O-C- symmetric stretching, near 900 cm-1 (strong absorption band)

Larger rings 1. C-O-C stretching vibration: -C-O-C- stretching, near 1100 cm-1 (strong absorption band) In most instances, when used alone, strong absorption at the cited regions is considered to be related to the stretching vibration of only a C-O- link. Another absorption feature of the spectrum should be taken into consideration when using the C-O- absorption band as indicative of an ether group. For example, the absence of characteristic absorption features of those functional groups which contain the C-O- link (alcohol groups, ester groups, etc.) increases the probability of the C-Oabsorption as indicative of an ether group.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Alcohols Primary 1. O-H stretching vibration: O-H stretching (free), 3650-3590 cm-1 (sharp medium strong intensity) OH stretching (interrmolecular H-bonds, dimeric), near 3500 cm-1 (broad strong intensity) OH stretching (intermolecular H-bonds, polymeric), near 3320 cm-1 (broad strong intensity) OH stretching (intramolecular H-bonds, single bridge), 3570-3450 cm-1 (broad) 2. C-OH stretching vibration: C-OH stretching, 1075-1000 cm-1 (limited diagnostic value) 3. O-H deformation vibration: O-H in-plane deformation, near 1400 cm-1 (limited diagnostic value)

Coming Soon! The absorption band location given for the C-OH stretching vibration of primary alcohols (1075-1000 cm-1) is not restricted to this class of alcohols alone. Some secondary alcohols, because of the environmental effect of neighboring structures on the -CHOH group, have a C-OH stretching vibration that cause absorption at the 1075 -1000 cm-1 region. As a consequence, the presence of a characteristic C-OH absorption band at the designated region in the spectra of alcohols has doubtful diagnostic value. It is valid as an indication of a primary alcohol group only when it can be supported by additional structural information. (See secondary alcohols.)

Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

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Alcohols Primary 1. O-H stretching vibration: O-H stretching (free), 3650-3590 cm-1 (sharp medium strong intensity) OH stretching (interrmolecular H-bonds, dimeric), near 3500 cm-1 (broad strong intensity) OH stretching (intermolecular H-bonds, polymeric), near 3320 cm-1 (broad strong intensity) OH stretching (intramolecular H-bonds, single bridge), 3570-3450 cm-1 (broad) 2. C-OH stretching vibration: C-OH stretching, 1075-1000 cm-1 (limited diagnostic value) 3. O-H deformation vibration: O-H in-plane deformation, near 1400 cm-1 (limited diagnostic value) The absorption band location given for the C-OH stretching vibration of primary alcohols (1075-1000 cm-1) is not restricted to this class of alcohols alone. Some secondary alcohols, because of the environmental effect of neighboring structures on the -CHOH group, have a C-OH stretching vibration that cause absorption at the 1075 -1000 cm-1 region. As a consequence, the presence of a characteristic C-OH absorption band at the designated region in the spectra of alcohols has doubtful diagnostic value. It is valid as an indication of a primary alcohol group only when it can be supported by additional structural information. (See secondary alcohols.)

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

Go to: home • ir • proton nmr • carbon nmr • mass spec

Alcohols Primary 1. O-H stretching vibration: O-H stretching (free), 3650-3590 cm-1 (sharp medium strong intensity) OH stretching (interrmolecular H-bonds, dimeric), near 3500 cm-1 (broad strong intensity) OH stretching (intermolecular H-bonds, polymeric), near 3320 cm-1 (broad strong intensity) OH stretching (intramolecular H-bonds, single bridge), 3570-3450 cm-1 (broad) 2. C-OH stretching vibration: C-OH stretching, 1075-1000 cm-1 (limited diagnostic value) 3. O-H deformation vibration: O-H in-plane deformation, near 1400 cm-1 (limited diagnostic value) The absorption band location given for the C-OH stretching vibration of primary alcohols (1075-1000 cm-1) is not restricted to this class of alcohols alone. Some secondary alcohols, because of the environmental effect of neighboring structures on the -CHOH group, have a C-OH stretching vibration that cause absorption at the 1075 -1000 cm-1 region. As a consequence, the presence of a characteristic C-OH absorption band at the designated region in the spectra of alcohols has doubtful diagnostic value. It is valid as an indication of a primary alcohol group only when it can be supported by additional structural information. (See secondary alcohols.)

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

Go to: home • ir • proton nmr • carbon nmr • mass spec

Alcohols Primary 1. O-H stretching vibration: O-H stretching (free), 3650-3590 cm-1 (sharp medium strong intensity) OH stretching (interrmolecular H-bonds, dimeric), near 3500 cm-1 (broad strong intensity) OH stretching (intermolecular H-bonds, polymeric), near 3320 cm-1 (broad strong intensity) OH stretching (intramolecular H-bonds, single bridge), 3570-3450 cm-1 (broad) 2. C-OH stretching vibration: C-OH stretching, 1075-1000 cm-1 (limited diagnostic value) 3. O-H deformation vibration: O-H in-plane deformation, near 1400 cm-1 (limited diagnostic value) The absorption band location given for the C-OH stretching vibration of primary alcohols (1075-1000 cm-1) is not restricted to this class of alcohols alone. Some secondary alcohols, because of the environmental effect of neighboring structures on the -CHOH group, have a C-OH stretching vibration that cause absorption at the 1075 -1000 cm-1 region. As a consequence, the presence of a characteristic C-OH absorption band at the designated region in the spectra of alcohols has doubtful diagnostic value. It is valid as an indication of a primary alcohol group only when it can be supported by additional structural information. (See secondary alcohols.)

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

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Go to: home • ir • proton nmr • carbon nmr • mass spec

Secondary Alcohols 1. O-H stretching vibration: O-H stretching (free), 3650-3590 cm-1 (sharp medium strong intensity) O-H stretching (intermolecular H-bonds, dimeric), near 3500 cm-1 (broad strong intensity) O-H stretching (intermolecular H-bonds, polymeric, near 3320 cm-1 (broad strong intensity) O-H stretching (intramolecular H-bonds, single bridge), 3570-3450 cm-1 (broad) 2. C-OH stretching vibration: Aliphatic saturated secondary alcohols C-OH stretching, 1125-1090 cm-1 Secondary alcohols having a C—OH stretching vibration that absorbs in the range cited for primary alcohols: alpha, beta- unsaturated secondary alcohols C-OH stretching, 1074-1012 cm-1 alpha-chloro or bromo secondary alcohols C-OH stretching, near 1050 cm-1 Aromatic secondary alcohols C-OH stretching, 1075- 1000 cm-1 Alicyclic secondary alcohols (5 membered ring and larger) C-OH stretching, 1090-1025 cm-1 C-OH stretching (equatorial), 1065-1037 cm-1 C-OH stretching (axial), 1036-970 cm-1 Sterols and steroids C-OH stretching, 1075-1000 cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

3. O-H deformation vibration: O-H in-plane deformation, near 1400 cm-1 (limited diagnostic value)

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Secondary Alcohols 1. O-H stretching vibration: O-H stretching (free), 3650-3590 cm-1 (sharp medium strong intensity) O-H stretching (intermolecular H-bonds, dimeric), near 3500 cm-1 (broad strong intensity) O-H stretching (intermolecular H-bonds, polymeric, near 3320 cm-1 (broad strong intensity) O-H stretching (intramolecular H-bonds, single bridge), 3570-3450 cm-1 (broad) 2. C-OH stretching vibration: Aliphatic saturated secondary alcohols C-OH stretching, 1125-1090 cm-1 Secondary alcohols having a C—OH stretching vibration that absorbs in the range cited for primary alcohols: alpha, beta- unsaturated secondary alcohols C-OH stretching, 1074-1012 cm-1 alpha-chloro or bromo secondary alcohols C-OH stretching, near 1050 cm-1 Aromatic secondary alcohols C-OH stretching, 1075- 1000 cm-1 Alicyclic secondary alcohols (5 membered ring and larger) C-OH stretching, 1090-1025 cm-1 C-OH stretching (equatorial), 1065-1037 cm-1 C-OH stretching (axial), 1036-970 cm-1 Sterols and steroids C-OH stretching, 1075-1000 cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

3. O-H deformation vibration: O-H in-plane deformation, near 1400 cm-1 (limited diagnostic value)

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Secondary Alcohols 1. O-H stretching vibration: O-H stretching (free), 3650-3590 cm-1 (sharp medium strong intensity) O-H stretching (intermolecular H-bonds, dimeric), near 3500 cm-1 (broad strong intensity) O-H stretching (intermolecular H-bonds, polymeric, near 3320 cm-1 (broad strong intensity) O-H stretching (intramolecular H-bonds, single bridge), 3570-3450 cm-1 (broad) 2. C-OH stretching vibration: Aliphatic saturated secondary alcohols C-OH stretching, 1125-1090 cm-1 Secondary alcohols having a C—OH stretching vibration that absorbs in the range cited for primary alcohols: alpha, beta- unsaturated secondary alcohols C-OH stretching, 1074-1012 cm-1 alpha-chloro or bromo secondary alcohols C-OH stretching, near 1050 cm-1 Aromatic secondary alcohols C-OH stretching, 1075- 1000 cm-1 Alicyclic secondary alcohols (5 membered ring and larger) C-OH stretching, 1090-1025 cm-1 C-OH stretching (equatorial), 1065-1037 cm-1 C-OH stretching (axial), 1036-970 cm-1 Sterols and steroids C-OH stretching, 1075-1000 cm-1

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3. O-H deformation vibration: O-H in-plane deformation, near 1400 cm-1 (limited diagnostic value)

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Tertiary Alcohols 1. O-H stretching vibration: O-H stretching (free), 3650-3590 cm-1 (sharp medium strong intensity) O-H stretching (intermolecular H-bonds, dimeric), near 3500 cm-1 (broad strong intensity) O-H stretching (intermolecular H-bonds, polymeric), near 3320 cm-1 (broad strong intensity) O-H stretching (intramolecular H-bonds, single bridge), 3570-3450 cm-1 (broad) 2. C-OH stretching vibration. C-OH stretching, 1210-1100 cm-1 3. O-H deformation vibration: OH in-plane deformation, near 1400cm-1

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Tertiary Alcohols 1. O-H stretching vibration: O-H stretching (free), 3650-3590 cm-1 (sharp medium strong intensity) O-H stretching (intermolecular H-bonds, dimeric), near 3500 cm-1 (broad strong intensity) O-H stretching (intermolecular H-bonds, polymeric), near 3320 cm-1 (broad strong intensity) O-H stretching (intramolecular H-bonds, single bridge), 3570-3450 cm-1 (broad) 2. C-OH stretching vibration. C-OH stretching, 1210-1100 cm-1 3. O-H deformation vibration: OH in-plane deformation, near 1400cm-1

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Tertiary Alcohols 1. O-H stretching vibration: O-H stretching (free), 3650-3590 cm-1 (sharp medium strong intensity) O-H stretching (intermolecular H-bonds, dimeric), near 3500 cm-1 (broad strong intensity) O-H stretching (intermolecular H-bonds, polymeric), near 3320 cm-1 (broad strong intensity) O-H stretching (intramolecular H-bonds, single bridge), 3570-3450 cm-1 (broad) 2. C-OH stretching vibration. C-OH stretching, 1210-1100 cm-1 3. O-H deformation vibration: OH in-plane deformation, near 1400cm-1

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Diols 1. O-H stretching vibration: O-H stretching, 3300 cm-1 (very strong intensity, broad) 2. O-H in-plane deformation vibration: O-H deformation, 1450-1330 cm-1 (medium intensity) 3. C-O stretching vibration: C-O stretching, 1100-1000 cm-1 (one or more intense bands) The pattern of bands in the fingerprint are below 1250 cm-1 can serve as a key to the identification of these compounds.

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Carbohydrates 1. O-H stretching vibration: O-H stretching, 3300 cm-1 (very strong intensity, broad) 2. O-H in-plane deformation vibration: O-H deformation,1450-1330 cm-1 (medium intensity) 3. C-O stretching vibration: C-O stretching, 1100-1000 cm-1 (one or more intense bands) The pattern of bands in the fingerprint are below 1250 cm-1 can serve as a key to the identification of these compounds.

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Phenols 1. O-H stretching vibration: O-H stretching (free), 3650-3590 cm-1 (sharp) O-H stretching (intermolecular H-bonds, dimeric), near 3500 cm-1 (broad strong intensity) O-H stretching (intermolecular H-bonds, polymeric), near 3320 cm-1 (broad strong intensity) O-H stretching (intramolecular H-bonds, single bridge), 3570-3450 cm-1 (broad) 2. C-OH stretching vibration: C-OH stretching, 1260-1180 cm-1 3. O-H deformation vibration: O-H deformation,1390-1330 cm-1 (medium intensity) Increases in the strength of H-bonds are accompanied by shifts to lower frequencies of the absorption bands due to O-H stretching vibration. The occurrence of multiple absorption bands at the O-H stretching region in the spectra of samples examined in the neat or solid form is indicative of an involvement of the OH group in more than one type of hydrogen bonding.

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Ketones Aliphatic Open Chain Ketones 1. C=O stretching vibration: C=O stretching, saturated, 1725-1705 cm-1 C=O stretching, alpha,beta-unsaturated, 1690-1675 cm-1 2. C-C-C stretching vibration: C-C-C asymmetric stretching, 1230-1100 cm-1 3. C-H bending vibration of CH3 when attached to C=O: CH3 bending symmetric, methyl ketones (abnormally strong absorption band)

1370-1350 cm-1

Aliphatic Cyclic Ketones 1. C=O stretching vibration: C=O stretching, 4 membered ring, about 1775 cm-1 C=O stretching, 5 membered ring, 1750-1740 cm-1 C=O stretching, 6 and 7 membered ring, 1745-1725 cm-1

Aryl Ketones 1. C=O stretching vibration: C=O stretching, 1690-1680 cm-1 C=O stretching, diaryI ketones, 1670-1660 cm-1

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2. C—C—C stretching vibration: C-C-C asymmetric stretching, 325-1215 cm1

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Ketones Aliphatic Open Chain Ketones 1. C=O stretching vibration: C=O stretching, saturated, 1725-1705 cm-1 C=O stretching, alpha,beta-unsaturated, 1690-1675 cm-1 2. C-C-C stretching vibration: C-C-C asymmetric stretching, 1230-1100 cm-1 3. C-H bending vibration of CH3 when attached to C=O: CH3 bending symmetric, methyl ketones (abnormally strong absorption band)

1370-1350 cm-1

Aliphatic Cyclic Ketones 1. C=O stretching vibration: C=O stretching, 4 membered ring, about 1775 cm-1 C=O stretching, 5 membered ring, 1750-1740 cm-1 C=O stretching, 6 and 7 membered ring, 1745-1725 cm-1

Aryl Ketones 1. C=O stretching vibration: C=O stretching, 1690-1680 cm-1 C=O stretching, diaryI ketones, 1670-1660 cm-1

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2. C—C—C stretching vibration: C-C-C asymmetric stretching, 325-1215 cm1

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Ketones Aliphatic Open Chain Ketones 1. C=O stretching vibration: C=O stretching, saturated, 1725-1705 cm-1 C=O stretching, alpha,beta-unsaturated, 1690-1675 cm-1 2. C-C-C stretching vibration: C-C-C asymmetric stretching, 1230-1100 cm-1 3. C-H bending vibration of CH3 when attached to C=O: CH3 bending symmetric, methyl ketones (abnormally strong absorption band)

1370-1350 cm-1

Aliphatic Cyclic Ketones 1. C=O stretching vibration: C=O stretching, 4 membered ring, about 1775 cm-1 C=O stretching, 5 membered ring, 1750-1740 cm-1 C=O stretching, 6 and 7 membered ring, 1745-1725 cm-1

Aryl Ketones 1. C=O stretching vibration: C=O stretching, 1690-1680 cm-1 C=O stretching, diaryI ketones, 1670-1660 cm-1

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2. C—C—C stretching vibration: C-C-C asymmetric stretching, 325-1215 cm1

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α- and β- Diketones α-Diketones 1. C=O stretching vibration: C=O stretching,1730-1710 cm-1 (strong) 2. CH3 symmetric deformation: CH3 deformation,1360-1355 cm-1

β-Diketones (Enolic forms) 1. -OH stretching vibration (hydrogen bonded): OH stretching, 2900-2000 cm-1 2. C=O and C=C stretching vibrations: C=O stretching and C=C stretching, 1670-1530 cm-1 Other vibrations similar to mono-ketones.

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Aldehydes 1. C(=O)-H stretching vibration: CH stretching, 2 sharp bands of medium intensity near 2941 cm-1 and 2720 cm-1 2. C(=O) stretching vibration: C=O stretching, 1725-1715 cm-1 (strong) 3. C(=O)-H deformation vibration: C-H deformation, 900-700 cm-1 (limited diagnostic value)

Aromatic and Unsaturated Aliphatic 1. C=O stretching vibration: C=O stretching, near 1695 cm-1

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Acid Halides Aliphatic Acid Halides 1. C=O stretching vibration: C=O stretching, 1810-1795 cm-1 (strong absorption band) 2. C-C= stretching vibration: -C-C= stretching, 965-920 cm-1 (medium strong absorption band)

Aromatic Acid Halides, C=O link attached to C atom of side chain 1. C=O stretching vibration: C=O stretching, 1810-1795 cm-1 (strong absorption band) 2. C-C= stretching vibration: -C-C= stretching, 965-920 cm-1 (medium strong absorption band)

Aromatic Acid Halides, C=O link attached to C atom of aromatic ring 1. C=O stretching vibration: C=O stretching, 1785-1765 cm-1 (strong absorption band)

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The relatively high wave number location of the C=O absorption band, due to the substitution of a halogen on the carbon atom of the C=O link, is a characteristic feature of this class of substances. Substitution of a halogen on the alpha carbon shifts the C=O absorption band to a slightly higher wave number location, while conjugation of the C=O link with an alpha, beta double bond or aryl group shifts the C=O absorption band to slightly lower wave number locations. When the absorption spectra of aryl acid halides show two bands at the C=O absorption region, the second band can be attributed to a low lying fundamental that is influenced by Fermi resonance.

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Anhydrides Acyclic Anhydrides 1. C=O stretching vibration: C=O stretching, two bands, 1850-1800 cm-1 1790 - 1740 cm1

(the stronger of the two absorption bands) 2. C-O-C stretching vibration: -C-O-C- stretching, 1175-1045 cm-1 (strong broad absorption)

Cyclic Anhydrides (5 membered rings); 1. C=O stretching vibration: C=O stretching, two bands,1870-1820 cm1

1800-1750 cm1

(the weaker of the two absorption bands) 2. C-O-C stretching vibration: -C-O-C- stretching,1310-1210 cm-1 The substitution of a halogen on the alpha carbon causes the C=O absorption bands to shift to a slightly higher wave number location (F>CI>Br>l). Conjugation of the C=O links with alpha, beta double bonds or aryl groups shift the C=O absorption bands to slightly lower wave number locations.

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Primary Amides 1. NH2 stretching vibrations (symmetric and asymmetric): NH stretching, near 3350 cm-1 NH stretching, near 3180 cm-1 2. C=O stretching vibration: C=O stretching, 1680-1650 cm-1 3. NH2 rocking vibration: NH2 rocking, 1650-1625 cm-1 (strong absorption bands usually overlapping with C=O stretch) 4. A fifth distinct band occurs in the range from 1420-1400 cm-1 but is of limited diagnostic value since it is observed in the spectra of other carbonyl compounds.

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Secondary Amides 1. N-H stretching vibration: NH stretching, near 3270 cm-1 2. C=O stretching vibration: C=O stretching, 1680-1630 cm-1 (very strong intensity) 3. Combination of N-H deformation and C-N stretching vibrations: NH deformation and C-N stretching, 1570-1515 cm-1 (strong intensity) 4. Mixed C-N stretching and N-H bending vibrations: C-N stretching and N-H bending, 1310-1200 cm-1

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Tertiary Amides 1 C=O stretching vibration: C=O stretching, 1670-1630 cm-1 (very strong intensity) When present, aliphatic -N(CH3)2 groups show two absorption bands near 2820 cm-1 and 2760 cm-1, and aromatic -N(CH3)2 groups give rise to one absorption band near 2820 cm-1. However, since the asymmetric and symmetric stretching vibrations of CH2 and CH3 groups normally absorb from 2960-2850 cm-1, the absorption effect of the CH2 and CH3 groups attached to the amide nitrogen is not always easy to detect.

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Imides 1. N-H stretching vibration: N-H stretching, near 3220 cm-1 (A strong band similar to that of lactams and secondary amides.) 2. C=O stretching vibration: C=O stretching, 1750-1670 cm-1 (A very strong band, usually split into a doublet or triplet.) 3. Combined C—N stretching and N—H bending vibrations: C-N stretching and N-H bending, 1310--1210 cm-1 (strong)

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Hydrazides Generally similar to the corresponding amides. 1. NH2 stretching vibration: NH2 stretching, 3450-3150 cm-1 2. C=O stretching vibration: C=O stretching, near 1640 cm-1 3. Combination of N-H deformation and C-N stretching vibrations: -1 N-H deformation and C-N stretching, near 1540 cm

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Ureas In general similar to the corresponding amides. 1. N-H and NH2 stretching vibrations: N-H stretching and NH2 stretching, 3360-3170 cm-1 2. C=O stretching vibrations: C=O stretching, 1690-1630 cm-1 (strong intensity)

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Hydantoins 1. N-H stretching vibrations: -1 N-H stretching, 3300-3120 cm 2. C=O stretching vibrations: -1 C=O stretching, 1750-1670 cm 3. C-N stretching and NH bending vibrations: -1 C-N stretching and NH bending, 1310-1210 cm

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Carboxylic Acids Aliphatic Open Chain Carboxylic Acids 1. C=O stretching vibration: C=O stretching, saturated, 1725-1700 cm-1 C=O stretching, αβ-unsaturated, 1705-1690 cm-1 C=O, α-halogen substituted,1740-1705 cm-1 2. O-H stretching vibration: OH stretching, H-bonded in dimerized acids, 3000-2500 cm-1 (broadband) 3. O-H deformation vibration: O-H out-of-plane deformation, H-bonded in dimerized acids, 950-900 cm-1 4. Coupled C-O stretching vibration and O-H deformation vibrations: C-O stretching and OH in-plane deformation, coupled, near 1430 cm-1 and near 1300 cm-1 (two bands) 5. C-H deformation of CH2 adjacent to C=O; CH2 bending, near 1410 cm-1 6. C-H rocking and twisting vibration of CH2 groups in long chain acids: CH2 rocking and twisting, crystalline fatty acids: 1350-1180 cm-1 (the number of bands increases as the number of consecutive CH2 groups increase)

Aryl Carboxylic Acids

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1. C=O stretching vibration: C=O stretching, 1700-1680 cm-1 C=O stretching, internally bonded, 1670-1650 cm-1 2. O-H stretching vibration: OH stretching, H-bonded in dimerized acids, 3000-2500 cm-1 (broadband) 3. O-H deformation vibration: OH out-of-plane deformation, H-bonded in dimerized acids, 950-900 cm-1 4. Coupled C-O stretching vibration and O-H deformation vibrations: C-O stretching and O-H in-plane deformation, coupled, near 1430 cm-1 and near 1300 cm-1 (two bands)

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Carboxylic Acids Aliphatic Open Chain Carboxylic Acids 1. C=O stretching vibration: C=O stretching, saturated, 1725-1700 cm-1 C=O stretching, αβ-unsaturated, 1705-1690 cm-1 C=O, α-halogen substituted,1740-1705 cm-1 2. O-H stretching vibration: OH stretching, H-bonded in dimerized acids, 3000-2500 cm-1 (broadband) 3. O-H deformation vibration: O-H out-of-plane deformation, H-bonded in dimerized acids, 950-900 cm-1 4. Coupled C-O stretching vibration and O-H deformation vibrations: C-O stretching and OH in-plane deformation, coupled, near 1430 cm-1 and near 1300 cm-1 (two bands) 5. C-H deformation of CH2 adjacent to C=O; CH2 bending, near 1410 cm-1 6. C-H rocking and twisting vibration of CH2 groups in long chain acids: CH2 rocking and twisting, crystalline fatty acids: 1350-1180 cm-1 (the number of bands increases as the number of consecutive CH2 groups increase)

Aryl Carboxylic Acids

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1. C=O stretching vibration: C=O stretching, 1700-1680 cm-1 C=O stretching, internally bonded, 1670-1650 cm-1 2. O-H stretching vibration: OH stretching, H-bonded in dimerized acids, 3000-2500 cm-1 (broadband) 3. O-H deformation vibration: OH out-of-plane deformation, H-bonded in dimerized acids, 950-900 cm-1 4. Coupled C-O stretching vibration and O-H deformation vibrations: C-O stretching and O-H in-plane deformation, coupled, near 1430 cm-1 and near 1300 cm-1 (two bands)

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Carboxylic Acids Aliphatic Open Chain Carboxylic Acids 1. C=O stretching vibration: C=O stretching, saturated, 1725-1700 cm-1 C=O stretching, αβ-unsaturated, 1705-1690 cm-1 C=O, α-halogen substituted,1740-1705 cm-1 2. O-H stretching vibration: OH stretching, H-bonded in dimerized acids, 3000-2500 cm-1 (broadband) 3. O-H deformation vibration: O-H out-of-plane deformation, H-bonded in dimerized acids, 950-900 cm-1 4. Coupled C-O stretching vibration and O-H deformation vibrations: C-O stretching and OH in-plane deformation, coupled, near 1430 cm-1 and near 1300 cm-1 (two bands) 5. C-H deformation of CH2 adjacent to C=O; CH2 bending, near 1410 cm-1 6. C-H rocking and twisting vibration of CH2 groups in long chain acids: CH2 rocking and twisting, crystalline fatty acids: 1350-1180 cm-1 (the number of bands increases as the number of consecutive CH2 groups increase)

Aryl Carboxylic Acids

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1. C=O stretching vibration: C=O stretching, 1700-1680 cm-1 C=O stretching, internally bonded, 1670-1650 cm-1 2. O-H stretching vibration: OH stretching, H-bonded in dimerized acids, 3000-2500 cm-1 (broadband) 3. O-H deformation vibration: OH out-of-plane deformation, H-bonded in dimerized acids, 950-900 cm-1 4. Coupled C-O stretching vibration and O-H deformation vibrations: C-O stretching and O-H in-plane deformation, coupled, near 1430 cm-1 and near 1300 cm-1 (two bands)

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Amino Acids

Zwitterionic Form.

1.

stretching vibration:

asymmetric stretching, 1600-1560 cm-1

Coming Soon!

symmetric stretching, near 1410 cm-1

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2. NH3+ stretching vibration: NH3+ asymmetric stretching, 3130-3030 cm-1 NH3+ symmetric stretching, 3000-2000 cm-1 3. NH3+ deformation vibration: NH3+ asymmetric deformation, 1660-1600 cm-1 (usually weak absorption band, when present) NH3+ symmetric deformation, 1570-1550 cm-1 4. C-N stretching vibration: C-N stretching,1040-1000 cm-1

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Salts of Carboxylic Acids 1. C=O asymmetric stretching vibration: C=O asymmetric stretching, 1610-1560 cm-1 (A very strong band due to the asymmetric stretching mode of CO2 unit, it usually shows splitting in the spectra of calcium and lithium salts. 2. C=O symmetric stretching vibration: C=O symmetric stretching, 1400-1300 cm-1 (A broad, intense band which is not always sharply resolved into several subpeaks.)

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Aliphatic and Olefinic Esters 1. C=O stretching vibration: C=O stretching, 1744-1739 cm-1 (very strong intensity) Vinyl and phenyl esters, near 1770 cm-1 Esters of α and β unsaturated acids, near 1720 cm-1 2. C-O-C stretching vibration: C-O-C stretching, 1280-1100 cm-1 (usually accompanied by one or more weaker bands in the region from 1300-1000 cm-1). Formates near 1185 cm-1 Acetates near 1256 cm-1 Propionates near 1194 cm-1 n-Butyrates near 1200 cm-1 3. Overtone of C=O stretching vibration - A weak band near 3450 cm-1 4. CH2 wagging vibration: CH2 wagging, 1345-1180 cm-1

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Aliphatic and Olefinic Esters 1. C=O stretching vibration: C=O stretching, 1744-1739 cm-1 (very strong intensity) Vinyl and phenyl esters, near 1770 cm-1 Esters of α and β unsaturated acids, near 1720 cm-1 2. C-O-C stretching vibration: C-O-C stretching, 1280-1100 cm-1 (usually accompanied by one or more weaker bands in the region from 1300-1000 cm-1). Formates near 1185 cm-1 Acetates near 1256 cm-1 Propionates near 1194 cm-1 n-Butyrates near 1200 cm-1 3. Overtone of C=O stretching vibration - A weak band near 3450 cm-1 4. CH2 wagging vibration: CH2 wagging, 1345-1180 cm-1

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Aliphatic and Olefinic Esters 1. C=O stretching vibration: C=O stretching, 1744-1739 cm-1 (very strong intensity) Vinyl and phenyl esters, near 1770 cm-1 Esters of α and β unsaturated acids, near 1720 cm-1 2. C-O-C stretching vibration: C-O-C stretching, 1280-1100 cm-1 (usually accompanied by one or more weaker bands in the region from 1300-1000 cm-1). Formates near 1185 cm-1 Acetates near 1256 cm-1 Propionates near 1194 cm-1 n-Butyrates near 1200 cm-1 3. Overtone of C=O stretching vibration - A weak band near 3450 cm-1 4. CH2 wagging vibration: CH2 wagging, 1345-1180 cm-1

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Aromatic Esters 1. C=O stretching vibration: C=O stretching (Benzoates), 1735-1720 cm-1 C=O stretching (Phenyl ester), near 1770 cm-1 2. C-O-C stretching vibrations: C-O-C stretching (Benzoates), 1290 cm-1and 1110 cm-1 C-O-C stretching (Phthalates), 1300 - 1250 cm-1and a pattern of three bands in the 1100 - 1000 cm-1region.

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Aromatic Esters 1. C=O stretching vibration: C=O stretching (Benzoates), 1735-1720 cm-1 C=O stretching (Phenyl ester), near 1770 cm-1 2. C-O-C stretching vibrations: C-O-C stretching (Benzoates), 1290 cm-1and 1110 cm-1 C-O-C stretching (Phthalates), 1300 - 1250 cm-1and a pattern of three bands in the 1100 - 1000 cm-1region.

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

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Lactones 1. C=O stretching vibration: C=O stretching (Benzoates), 1735-1720 cm-1 C=O stretching (Phenyl ester), near 1770 cm-1 2. C-O-C stretching vibrations: C-O-C stretching (Benzoates), 1290 cm-1and 1110 cm-1 C-O-C stretching (Phthalates), 1300 - 1250 cm-1and a pattern of three bands in the 1100 - 1000 cm-1region.

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

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Chloroformates 1. C=O stretching vibration: C=O stretching, 1744-1739 cm-1 (very strong intensity) Vinyl and phenyl esters, near 1770 cm-1 Esters of α and β unsaturated acids, near 1720 cm-1 2. C-O-C stretching vibration: C-O-C stretching, 1280-1100 cm-1 (usually accompanied by one or more weaker bands in the region from 1300-1000 cm-1). Formates near 1185 cm-1 Acetates near 1256 cm-1 Propionates near 1194 cm-1 n-Butyrates near 1200 cm-1 3. Overtone of C=O stretching vibration - A weak band near 3450 cm-1 4. CH2 wagging vibration: CH2 wagging, 1345-1180 cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

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Esters of Thio-Acids 1. C=O stretching vibration: C=O stretching, 1744-1739 cm-1 (very strong intensity) Vinyl and phenyl esters, near 1770 cm-1 Esters of α and β unsaturated acids, near 1720 cm-1 2. C-O-C stretching vibration: C-O-C stretching, 1280-1100 cm-1 (usually accompanied by one or more weaker bands in the region from 1300-1000 cm-1). Formates near 1185 cm-1 Acetates near 1256 cm-1 Propionates near 1194 cm-1 n-Butyrates near 1200 cm-1 3. Overtone of C=O stretching vibration - A weak band near 3450 cm-1 4. CH2 wagging vibration: CH2 wagging, 1345-1180 cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

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Carbamates 1. C=O stretching vibration: C=O stretching, 1744-1739 cm-1 (very strong intensity) Vinyl and phenyl esters, near 1770 cm-1 Esters of α and β unsaturated acids, near 1720 cm-1 2. C-O-C stretching vibration: C-O-C stretching, 1280-1100 cm-1 (usually accompanied by one or more weaker bands in the region from 1300-1000 cm-1). Formates near 1185 cm-1 Acetates near 1256 cm-1 Propionates near 1194 cm-1 n-Butyrates near 1200 cm-1 3. Overtone of C=O stretching vibration - A weak band near 3450 cm-1 4. CH2 wagging vibration: CH2 wagging, 1345-1180 cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

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Esters of Phosphorus Acids 1. C=O stretching vibration: C=O stretching, 1744-1739 cm-1 (very strong intensity) Vinyl and phenyl esters, near 1770 cm-1 Esters of α and β unsaturated acids, near 1720 cm-1 2. C-O-C stretching vibration: C-O-C stretching, 1280-1100 cm-1 (usually accompanied by one or more weaker bands in the region from 1300-1000 cm-1). Formates near 1185 cm-1 Acetates near 1256 cm-1 Propionates near 1194 cm-1 n-Butyrates near 1200 cm-1 3. Overtone of C=O stretching vibration - A weak band near 3450 cm-1 4. CH2 wagging vibration: CH2 wagging, 1345-1180 cm-1

Coming Soon! Click on a vibrational mode link in the table to the left or the spectrum above to visualize the vibrational mode here.

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The Sadtler Handbook of Proton NMR Spectra

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Saturated Hydrocarbons Normal Alkanes

The normal alkanes are an easily recognized group of compounds consisting of two higher order bands resonating in a narrow chemical shift range at high field.

Chemical Shifts (CH2)n CH3

near 1.3 ppm - a complex multiplet in the shorter (C4, C5, C6) alkanes gradually becoming a broad, single peak as the number of carbons in the chain increases. near 0.9 ppm - a distorted triplet

Due to the higher order patterns which result from the very narrow chemical shift range, it is not possible to measure accurately the vicinal coupling constants (H-C-C-H). However, because the distorted triplet at 0.9 ppm is nearly identical to those observed for the substituted alkanes, it would appear that the coupling constants are similar to those of the substituted alkanes, i.e. J H-C-C-H = 6-8 Hz.

Solubility and Solvent Effects The normal alkanes, as indeed all of the hydrocarbons, are most readily soluble in the halogenated solvents, CCI4 and CDCI3. Their solubility in even these liquids decreases markedly as the molecular weight (chain length) increases beyond molecular weight 200 (C12 to C15). Allowing the sample-solvent slurry to stand overnight, agitation of the mixture and warming, are helpful in obtaining higher sample solution concentrations.

Impurities Because most commercially available alkanes are obtained from the fractional distillation of petroleum, impurities such as the cyclic alkanes, and simple aromatic hydrocarbons such as toluene, ethyl benzene and the xylenes, may be observed in their NMR spectra.

Characterization Differentiating between the various alkanes is usually accomplished by careful measurement of the methyl and methylene integration values. Determinations accurate to within one carbon are routinely obtained with chain lengths up to about Triacontane (C30). Note: Other nuclei which possess a weak deshielding effect similar to that of hydrocarbon groups may produce spectra almost identical in appearance and chemical shift to those of the normal alkanes. Included in this group would be nuclei such as Phosphorus, Tin, Lead, Mercury, Boron and Silicon. Since many of these nuclei possess a spin greater than zero, their spectra may display isotope side-bands slightly above and/or below the primary chemical shift range of the sample. These isotope sidebands are helpful in determining that a high field pattern is not that of a normal alkane.

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Saturated Hydrocarbons Branched Alkanes

The presence of one or more branching groups along the hydrocarbon chain increases the complexity and chemical shift ranges of the branched alkanes in comparison to those of the normal alkanes. As a consequence of the larger number of methyl groups that are present, the intensity of the bands at higher field is increased.

Chemical Shifts The overall range of chemical shifts for the branched alkanes is 0.6-2.0 ppm, with the methyl (CH3) resonances on the higher field side, the methylene (CH2) resonances in the intermediate portion of the range and the methine (CH) groups resonating in the lower field area (1.3-2.0 ppm). Methyl Groups

0.8-0.95 ppm distorted triplet

broadened doublet

sharp singlet

Methylene and Methine Groups The methylene and methine groups are almost always complex, higher order, overlapping multiplets that cannot be easily characterized by first order approximations.

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As with the normal alkanes, higher order effects prevent the direct measurement of coupling constants, however, the separation of the peaks of methyl doublets indicates that the JH-C-C-H (vicinal) coupling constants are of the order of 6-9 Hz.

Solubility and Solvent Effects The branched alkanes are readily soluble in the halogenated hydrocarbons normally utilized as NMR solvents. The presence of branching groups makes the branched hydrocarbons more soluble than a normal hydrocarbon of comparable molecular weight.

Impurities Branched hydrocarbons obtained from petroleum sources may display impurities arising from the cyclic alkanes and low molecular weight aromatic hydrocarbons.

Characterization The branched alkanes are probably the most difficult compounds to identify without the aid of known reference spectra. These spectra do however produce unique "fingerprint" patterns which are well represented in the various collections of NMR reference spectra which are currently available. If the methyl, methylene and methine resonance bands are sufficiently well separated, a comparison of the integration values can be used to advantage in determining the relative number of the various types of carbon atoms present (methyl, methylene, methine).

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Saturated Hydrocarbons Cyclic Alkanes The cyclic alkanes produce both the simplest patterns (one single peak) for the unsubstituted parent rings, and the most complex, poorly resolved patterns, for the substituted derivatives. The three, four and five membered rings usually produce complex but relatively well resolved absorption patterns. The larger rings (C6 and higher) due to the slow interchange in ring shape produce poorly resolved, broad bands often covering more than a full one ppm, arising from the hydrogens attached to the ring carbons.

Alicyclic Protons

ppm

Compound

Solvent

0.22

(lit.)

1.96

(lit.)

1.50

CCl 4

1.42

CCl 4

1.53

CDCl 3

1.52

CCl 4

Coupling and Coupling Constants The spectral patterns of the cyclic alkanes are usually too complex or too poorly resolved to provide any useful measurements of the coupling constants.

Solubility and Solvent Effects http://www.knowitall.com/handbook/hnmr/saturated_hydrocarbons/cyclic/HNMR_Cyclic_Alkanes.htm（第 1／9 页）2005-10-1 21:42:36

The Sadtler Handbook of Proton NMR Spectra

Most representatives of the cyclic alkanes are readily soluble in the halogenated hydrocarbon solvents.

Characterization As with the branched alkanes, if the resonance bands are sufficiently well separated, then a comparison of the integration values may be useful. Generally, though, a comparison with known reference spectra will be found to be the most reliable method of identifying an unknown of this group.

Alicyclic Derivatives Substitution of the cyclic alkanes by a deshielding substituent leads to a characteristic chemical shift for the hydrogen attached to the alpha carbon depending upon the size of the ring and the deshielding effect of the substituting group as listed below.

Cyclopropane Derivatives (C3-X)

δ

b

(ppm)

(ppm)

δ a

-X

Solvent

0.1-0.7

0.98

CDCI 3

0.1-0.6

1.05

CCI4

0.2-0.9

1.10

0.3-0.8

1.29

CCI4

0.5-1.1

1.36

CDCI3

0.5-1.2

1.40

CDCI3

0.6-1.1

1.50

CCI 4

0.7-1.3

1.53

CCI 4

-CH2-NH2 HCl

D2O

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The Sadtler Handbook of Proton NMR Spectra

0.6-1.2

1.79

Polysol

0.7-1.1

1.97

CDCI3

0.4-1.2

2.00

CCI 4

0.9-1.5

2.07

CCI 4

0.2-0.7

2.31

0.5-1.2

2.49

CDCI

0.7-1.4

2.61

CDCI3

0.63,1.80

-NH 2

CDCI3

3

Polysol

3.35

With the exception of the last substituent on the list, the hydrogens bonded to the beta carbons produce a complex higher order pattern at thigh field.

Cyclobutane Derivatives (C4-X)

δ

b

(ppm)

δ

a

(ppm) -X

-CH2-OH

Solvent

1.4-2.3

2.50

CDCI3

1.7-2.5

3.08

CCI4

1.6-2.7

3.19

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

1.7-2.6

3.45

CDCI3

1.6-2.7

3.60

CCI4

1.5-2.6

3.85

1.6-2.7

3.95

1.1-2.5

4.16

-NH2 HCl

D2O CCI4

-OH

CDCI3

Cyclopentane Derivatives (C5—X)

δ

b

(ppm)

δ

a

(ppm) -X

-CH 2

Solvent

1.2-2.3

1.81

1.3-2.2

2.69

CCI4

1.6-2.2

2.70

CCI4

1.4-2.3

2.76

CDCI3

1.3-2.2

2.90

CDCI3

1.2-2.2

3.00

1.4-2.3

3.19

-NH-CH 3

CCI4

CDCI3 CCI 4

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The Sadtler Handbook of Proton NMR Spectra

1.0-2.1

3.31

-NH 2

CDCI3

1.3-2.2

3.65

1.1-2.2

4.19

1.3-2.2

4.21

-OH

CCI 4

1.3-2.4

4.32

-I

CCI

1.4-2.3

4.35

-Cl

CCI4

1.4-2.4

4.38

-Br

CCI4

1.1-2.1

4.49

CCI4

CDCI3

4

Polysol

Cyclohexane Derivatives (C6-X)

δ

b

(ppm)

δ

0.9-2.2

2.26

0.7-2.1

2.32

0.9-2.2

2.34

0.6-2.1

2.35

0.8-2.1

2.39

a

(ppm)

Solvent

-X

CCI4

-NH-R

2

CCI4 Polysol

-NH-CH

3

CDCI3 CCI4

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The Sadtler Handbook of Proton NMR Spectra

0.8-2.2

2.40

CDCI3

0.9-2.1

2.40

CCI4

0.8-2.1

2.42

CCI4

0.5-2.2

2.42

CCI4

0.7-2.1

2.49

CCI4

0.6-2.1

2.64

-NH 2

CCI4

1.2-2.1

2.64

-C≡N

CCI4

1.0-2.4

2.71

1.0-2.2

2.74

-SH

CCI4

1.0-2.5

2.92

-SO2-R

CDCI3

0.7-2.2

CCI4

-NH-SO2-NH-C6

Polysol

3.00 0.8-2.1

CDCI3 3.10

0.7-2.2

-N=C=N-C6

CDCI3

3.17 CDCI3

0.6-2.3 3.21

CDCI3

0.8-2.3 3.25

0.7-2.2

-O-R

CDCI3

3.27 0.6-2.2

Polysol 3.36

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The Sadtler Handbook of Proton NMR Spectra

0.9-2.2

CDCI3 3.46

1.0-2.2

-N=C=O

CDCI3

-OH

CCl4

-N≡C

CDCI3

3.48 0.8-2.1 3.49 1.0-2.2 3.60 0.7-2.3

CDCI3 3.70 CDCl3

0.8-2.2 3.79 0.9-2.8

-NH-SO2-OH

TFA

-Cl

CCI4

3.80 0.8-2.4 3.95 0.7-2.3

DMSO-d6 4.03

0.9-2.2

-OB(-O-C6)2

CDCI3

-Br

CCI4

-NO2

CCI4

-I

CDCI3

4.04 1.1-2.5 4.13 1.0-2.5 4.29 0.9-2.5 4.36 CCI4

0.9-2.2 4.71

CDCI3

1 .0-2. 1 4.76

0.9-2.3

-N(N=O)-C6

CDCI3

3.75, 4.83 0.9-2.2

CDCI3 4.89

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The Sadtler Handbook of Proton NMR Spectra

1.0-2.2

CCI4 4.95

1.1-2.4

CDCI3 5.16

Cycloheptane Derivatives

δ δ

c

(ppm)

1.80

b

(ppm)

1.80

δ

a

(ppm) -X

Solvent

CDCI3

2.53

-C≡N

CCI4

1.3-2.3

1.3-2.3

2.78

1.0-2.2

1.0-2.2

2.92

1.2-2.2

1.2-2.2

3.80

ca 1 .66

2.10

3.85

TFA

1.2-1.8

1.90

3.86

CDCI3

ca 1.61

2.00

4.10

ca 1.53

2.17

4.33

-NH2

-OH

-Cl

-Br

CDCI3

CDCI3

CCI4

CDCI3

Cyclooctane Derivatives

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The Sadtler Handbook of Proton NMR Spectra

δ δ

c

(ppm)

b

(ppm)

δ

a

(ppm)

Solvent -X

1.2-2.0

1.22.0

2.53

-NH-CH3

CDCI3

1.1-2.1

1.12.1

2.90

-NH2

CCI4

1.2-2.1

1.22.1

3.72

-OH

CCI4

1.4-2.2

1.42.2

3.88

ca 1.59

2.19

4.31

1.3-2.1

1.32.1

4.83

CCI4

ca 1 .59

1.85

5.09

CCI4

ca 1.59

1.85

5.15

CCI4

TFA

-Br

CCI4

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Unsaturated Hydrocarbons Acyclic Alkenes

No other type of organic compound produces such a wide variety of multiplet types over such a large chemical shift range as the acyclic alkenes. Proton-proton coupling through four bonds is common. Many samples are found to contain both cis and trans isomers producing a spectrum more complex than might be expected from a proposed structure. The olefinic double bond is a weak deshielder of both aliphatic and aromatic hydrogens often re-sulting in higher order, overlapping multiplets. The aliphatic chemical shift ranges below were abstracted from a large number of representative compounds.

Aliphatic Protons (General ranges)

δ c

(ppm)

0.9-1.0

δ b

(ppm)

δ a

(ppm)

-X

Solvent

1.6-2.0

CCl4, CDCl

(1.6-1.8)

CCl4, CDCI

0.9-1.3

1.9-2.1

CCl4, CDCl 3

1.3-1.7

1.9-2.2

CCl4, CDCl 3

(0.9-1.2)

1.9-2.7

CCl4, CDCl 3

(0.9-1.2)

3

3

CCl4, CDCl 3

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The Sadtler Handbook of Proton NMR Spectra

Coupling and Coupling Constants The wide variety of coupling constants observed in the spectra of the alkenes is quite helpful in determining the molecular arrangement of such structures and aid the analyst in differentiating the spectra of cis and trans isomers. The general coupling constant ranges provided below are the values observed for a large number of alkene compounds. Compound

J value J = 13-17 Hz

trans

J = 6-14 Hz

cis

J = 4-8 Hz J = 0-3 Hz

geminal

J = 0-2 Hz

Vinyl Compounds

trans (ppm)

cis (ppm)

(ppm)

δ

X

Solvent

a 5.10

5.01

5.79

CCl 4

4.82

4.78

5.80

CCl 4

5.53

6.20

6.00

CDCl 3

5.02

5.10

6.34

CCl 4

5.12

5.53

6.60

CDCl 3

5.04

5.50

6.62

CCl 4

4.43

4.74

7.18

CCl 4

4.49

4.80

7.23

CDCl 3

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The Sadtler Handbook of Proton NMR Spectra

trans (ppm)

cis (ppm)

δ a

X

(ppm)

Solvent

4.60

4.60

1.62

CCl 4

4.60

4.60

1.68

CCl 4

4.70

4.89

1.70

CCl 4

4.93

4.93

1.82

CCl 4

5.39

5.71

1.89

D2O

4.59

4.77

1.90

CCl 4

5.47

6.02

1.90

CCl 4

5.47

6.00

1.91

CCl 4

5.60

6.20

1.95

CCl 4

5.40

5.79

1.97

CDCl 3

1.98

CCl 4

ca 5.79 5.68

6.30

2.03

CDCl 3

5.01

5.31

2.10

CCl 4

1-Propenes

(ppm)

δ b

(ppm)

δ a

-X

Solvent

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The Sadtler Handbook of Proton NMR Spectra

1.91

CCl 4

4.6-6.0

CCl 4

1.93

2.07

CDCl

2.17

CCl 4

2.79

CDCl

3.10

CCl 4 CDCl

3.12

3.29

-S-S-R

3.30

-NH

2

3.33

3.63

3

4 CDCl 3 CCl 4

CCl 4

-I

CCl

3.88

-Br

CCl

3.99

-Cl

CCl

4.02

4.11

3

CCl

3.80

4.05

3

-OH

4 4

4 CDCl CCl 4 CDCl

4.48

CCl 4

4.60

CCl 4

4.62

CDCl

4.82

CCl 4

3

3

3

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The Sadtler Handbook of Proton NMR Spectra

2-Methyl Propenes

(ppm)

δ

δ

b

(ppm) a 1.85

-X

Solvent CCl 4

1.68 1.90

CDCl

3

1.75

1.69

1.98

1.69

2.01

1.70

2.00

1.62

2.11

-R 2 -CH 3 -R 5 -CH2-CH=CH 2

CCl 4 CCl 4 CCl 4 CDCl 3 CCl 4

-CH2-OH

CDCl 3 CCl 4

2.13 1.71 2.34

1.69

2.37 1.67

1.71

2.78

1.73

3.12

1.87

3.98

1.79

4.36

CCl 4

-NH 2 -Cl

CCl 4 CCl 4 CCl 4

1-Butenes

trans (ppm)

cis (ppm)

δ c

(ppm)

(ppm)

δ

(ppm)

δ

b

a

-X

Solvent

4.88

4.92

5.68

1.99

1.32

-CH 3

CCl

4.89

4.86

5.69

2.00

1.45

-R 11

CCl 4

4.87

4.91

5.68

2.05

1.45

-R 4

CCl

4.91

4.96

5.70

2.11

2.11

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4

4

CCl 4

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4.97

5.01

5.81

2.37

2.67

5.10

5.14

5.80

2.37

3.65

5.02

5.08

5.80

2.40

2.40

CDCl

-OH

CDCl 3 CDCl 3

2-Butenes

(ppm)

δ

(ppm)

δ

(ppm)

δ

-X

(ppm)

δ

Solvent

d

c

b

a

1.59

5.33

5.33

1.96

-R 2

CCl 4

1.59

5.31

5.31

1.97

-R 3

CCl 4

1.60

5.34

5.34

1.98

-CH

CCl 4

1.68

5.47

5.47

3.27

X-

δ d

(ppm)

δ c

(ppm)

δ b

3

CCl 4

(ppm)

δ a

-X

(ppm)

Solvent

3.07

5.63

5.63

3.07

Br-

3.99

6.01

6.01

3.07

-Br

CDCl 3

HO-

4.18

5.72

5.72

4.18

-OH

D2O

δ c

(ppm)

δ b

(ppm)

δ a

(ppm)

-X

3

CDCl 3

Solvent

1.53

4.27

5.82

CCl 4

1.74

5.35

5.35

CDCl 3

2.03

6.62

5.38

CDCl 3

Olefinic Protons http://www.knowitall.com/handbook/hnmr/unsaturated_hydrocarbons/acyclicalkenes/acyclicalkenes.html（第 6／10 页）2005-10-1 21:45:03

The Sadtler Handbook of Proton NMR Spectra

δ c

(ppm)

δ b

(ppm)

δ a

-X (all trans)

(ppm)

1.53 4.68

CCl 4

6.12

CCl 4

1.61

1.63

5.32

5.32

5.40

5.40

5.58

5.58

-R

CDCl

4

3 CDCl 3

1.63

CCl 4

1.78 5.91

6.21

1.80

CCl 4 6.00

6.34

CDCl 3

1.79 6.08

6.37

1.81

D2O

1.92

6.59

5.84

6.62

5.38

CDCl

6.70

6.00

6.80

6.04

7.01

5.84

CCl 4

2.00

1.90

CDCl

3

CCl 4

1.93 7.10

(ppm)

3

CCl 4

1.89

δ

Solvent

(ppm)

δ

5.91

-X

cis/trans

Solvent

b

a

7.35

5.53

cis

CDCl

7.71

5.86

trans

CDCl

http://www.knowitall.com/handbook/hnmr/unsaturated_hydrocarbons/acyclicalkenes/acyclicalkenes.html（第 7／10 页）2005-10-1 21:45:03

3 3

The Sadtler Handbook of Proton NMR Spectra

6.21

5.91

trans

6.11

-CH 3 -Cl

6.48 6.73

6.42

-Cl

trans

6.57

6.31

-CH2-OH

trans

4 CCl 4 CCl 4 CDCl

7.56

6.31

trans

CCl

7.60

6.38

trans

DMSO-d

7.80

6.43

trans

CDCl

7.71

6.45

trans

CDCl

7.02

6.61

trans

CCl

7.44

6.67

trans

CCl

7.52

6.67

trans

CDCl 3

7.60

6.82

trans

CDCl

7.79

6.91

trans

DMSO-d

7.70

7.02

trans

CDCl 3

7.79

7.29

trans

CDCl

7.97

7.45

trans

CDCl 3

X-

cis

-Br

(ppm)

δ

(ppm)

δ

b

a

CH3-

5.32

5.32

R7-

5.34

5.34

CCl

-X

-R

7

http://www.knowitall.com/handbook/hnmr/unsaturated_hydrocarbons/acyclicalkenes/acyclicalkenes.html（第 8／10 页）2005-10-1 21:45:03

3

4

6

3

3

4

4

3

6

3

Solvent

cis/trans

CDCl 3

cis

CCl 4

The Sadtler Handbook of Proton NMR Spectra

R2-

5.37

5.37

CH3-

5.45

5.45

5.79

6.98

5.89

7.46

CDCl 3

cis

6.00

7.64

CDCl 3

trans

6.24

6.48

Polysol

cis

6.25

6.25

CCl 4

cis

6.32

6.82

CDCl 3

6.59 or

7.03

CDCl3

6.64

6.64

6.83

6.83

7.04

7.04

Br-

Br-

-R

CCl 4 CDCl 3

2

-R 4

CDCl

-Br

trans trans

3

CCl

cis

4 CDCl 3

trans

CCl

trans

-Br

4

Aromatic Protons The aromatic patterns produced by the phenyl protons of alkene substituted benzenes are repre-sented by a wide variety of chemical shifts and patterns depending on the site and type of substituents on the C=C moiety. A relatively sharp single peak may be observed as high as 7.13 ppm (Cl-CH=CH-, trans) or as low as 7.54 ppm (Cl-SO2-CH=CH-). Generally, a complex band of overlapping multiplets is observed in the range from 7.1-7.6 ppm (CH2=CH-, CH2=C (CH3)-, R-C(=O)-CH=CH-). In at least one case, the ortho aromatic hydrogens are strongly deshielded in relation to the meta and para hydrogens producing two sets of bands, one at 7.55 and a range from 7.1-7.4 ppm (Cl-CH=CH-, cis). para substituted styrene derivatives

X

(ppm)

δ

CH3-OF-

6.65 6.90

para -X

(ppm)

δ

b

Solvent

a 7.08 7.23

-CH=CH-CH 3 -CH=CH 2

CCl

4 CDCl 3

http://www.knowitall.com/handbook/hnmr/unsaturated_hydrocarbons/acyclicalkenes/acyclicalkenes.html（第 9／10 页）2005-10-1 21:45:03

The Sadtler Handbook of Proton NMR Spectra

CH3-O-

6.76

7.22

Cl-

7.21

7.21

Cl-

7.23

-CH=CH 2 -CH=CH 2

7.23

-CH=CH 2

CCl 4 CCl 4 CDCl

3

Br-

7.34

7.12

Cl-

7.32

7.47

4 CDCl

7.28

7.68

Polysol

8.07

7.49

-CH=CH-CH2-OH

CCl

3

Polysol

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

http://www.knowitall.com/handbook/hnmr/unsaturated_hydrocarbons/acyclicalkenes/acyclicalkenes.html（第 10／10 页）2005-10-1 21:45:03

The Sadtler Handbook of Proton NMR Spectra

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Unsaturated Hydrocarbons Cyclic Alkenes

The cyclic alkenes are usually a relatively simple group to identify from their HNMR spectra. The spectra display three sets of resonance bands with the olefinic protons resonating in the range from 5-6 ppm, the methylene groups adjacent to the double bonds deshielded to about 2.1 ppm and the remaining methylene groups forming a separate band at slightly higher field. In the spectra of the smaller rings, cyclopentene and cyclohexene, the coupling constant between the aliphatic and olefinic hydrogens (CH2-CH=C) is quite small resulting in a single, slightly broadened peak for the olefinic hydrogens. As the ring sizes increase, this coupling constant increases in magnitude, to about 4 Hz for cycloheptene and about 5 Hz for cyclooctene.

(ppm)

δ

(ppm)

δ

d

(ppm)

δ

c

b

5.66

2.29

1.97

(1.85)

CCl 4

(1.62) 2

CCl 4

(1.64) 3

CCl 4

(1.53) 4

CCl 4

2.11

2.12 5.59

Solvent

1.97

2.11 5.71

-X

a

2.29

5.58

(ppm)

δ

2.12 (cis)

The deshielding effect of the olefinic bond on aliphatic groups bonded to it is similar to that observed for the acyclic alkenes, i.e. a weakly deshielding effect.

(ppm)

δ b

(ppm)

δ

-X

Ring system

Solvent

a

http://www.knowitall.com/handbook/hnmr/unsaturated_hydrocarbons/cyclicalkenes/cyclicalkenes.html（第 1／4 页）2005-10-1 21:47:08

The Sadtler Handbook of Proton NMR Spectra

CH3-

1.03

0.96

CCl 4

2.19

CH3-CH2-

CCl 4

1.60

CH3-

CCl 4

1.95

CH3-CH2-

CCl 4

The chemical shift changes brought about by substituents bonded to the various positions of the cyclic alkenes are often dramatic, particularly on the position-2 olefinic hydrogen. A series of monosubstituted compounds is listed below. Because of their smaller ring size, the cyclopentenes usually display two or three distinct bands at high field for the ring methylene groups depending on the position and deshielding effect of the substituent.

Cyclopentenes

(ppm)

δ 2.29

(ppm)

δ

δ

d

e 1.85

c 2.29

(1.5-2.5)

2.30

1.40

2.98

δ b 5.66

(ppm)

δ a

(ppm)

Compound

5.66

3.30

2.00

Solvent CCl 4

CCl 4

5.19

(1.0-2.5)

2.00

(ppm)

5.63

5.63

CCl 4

5.61

5.61

CCl 4

5.61

5.61

CCl 4

Cyclohexenes

http://www.knowitall.com/handbook/hnmr/unsaturated_hydrocarbons/cyclicalkenes/cyclicalkenes.html（第 2／4 页）2005-10-1 21:47:08

The Sadtler Handbook of Proton NMR Spectra

δ (ppm) 1.89

1.57

(ppm) d 1.57

2.09

1.72

1.72

1.88

1.60

1.98

δ

f

e

(ppm)

δ

δ c 1.89

(ppm)

δ b

(ppm)

δ a

(ppm)

Compound

Solvent

5.23

CCl 4

2.09

5.27

CCl 4

1.60

1.88

5.30

1.65

1.65

1.98

5.46

CCl 4 CCl 4

2.15

1.69

1.69

2.15

5.49

1.97

1.62

1.62

1.97

5.58

2.00

1.60

1.60

2.00

5.71

CCl 4

2.05

1.65

1.65

2.05

5.78

CDCl 3

2.22

1.68

1.68

2.22

6.58

CCl 4

2.28

1.68

1.68

2.28

7.11

CCl 4

2.32

1.69

1.69

2.32

7.39

CCl 4

CCl 4

5.58

3-Substituted Cyclohexenes

http://www.knowitall.com/handbook/hnmr/unsaturated_hydrocarbons/cyclicalkenes/cyclicalkenes.html（第 3／4 页）2005-10-1 21:47:08

CCl 4

The Sadtler Handbook of Proton NMR Spectra

δ (ppm) f

(ppm) e (1.1-2.5)

δ

δ d

(ppm)

δ c

(ppm)

δ b

(ppm)

δ a

(ppm)

-X

Solvent

5.56

5.56

CDCl 3

1.95

(1.3-1.9)

3.61

5.74

5.74

CCl 4

2.11

(1.3-2 .1)

4.78

5.80

5.80

CCl 4

4-Substituted Cyclohexenes

δ (ppm) f

(1.6-2.5)

(ppm)

δ e

(ppm) d (1.0-2.4)

δ

2.71

(1.6-2.8)

(1.6-2.6)

3.00

(ppm)

δ

(ppm)

δ

c

(ppm)

δ

b

a

Compound

Solvent

5.63

5.63

CDCl 3

5.65

5.65

CCl 4

5.66

5.66

CDCl 3

5.79

5.79

CCl 4

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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The Sadtler Handbook of Proton NMR Spectra

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Unsaturated Hydrocarbons Alkynes

The monosubstituted acetylenes (H-C≡C-X) are usually easily characterized because the acetylenic hydrogen appears over a relatively limited chemical shift range (2.0—3.0 ppm in CCl4) and displays coupling between non-equivalent proton groups on opposite sides of the triple bond linkage (J = 2.0-3.2 Hz). The absence of this hydrogen in the disubstituted acetylenes makes the identifi-cation of these compounds somewhat more difficult -although the coupling across the triple bond may still be observed. The deshielding effect of the C≡C linkage is similar to that of the C=C group, i.e., it is a weak deshielder of both aliphatic and aromatic protons.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Compound

1.80 0.93

Solvent CH3-C≡C-H

1.01

1.55

2.12

CH3-CH2-CH2-C≡C-H

1.40

1.53

2.11

CH3-CH2-CH2-CH2-C≡C-H

1.70

CDCl3 CCl4 CCl4 CCl4 CCl4

(1.18)

1..71

http://www.knowitall.com/handbook/hnmr/unsaturated_hydrocarbons/alkynes/alkynes.html（第 1／6 页）2005-10-1 21:49:45

CDCl3

The Sadtler Handbook of Proton NMR Spectra

2.32 1.01

CCl4

1.59

Monosubstituted ethynes

δ

a

(ppm)

-X

1.79

-R3

1.80

-CH3

2.25

-C(-CH3, -CH3, -R2)

Solvent CCl4 CDCl3 CCl4 CDCl3

2.29

2.30

-C(-CH3, -R2, -OH)

CCl4

2.33

-CH(-R2)-OH

CCl4

2.33

-CH(-R3)-OH

CCl4

2.37

CCl4

2.71

Polysol

2.86

CDCl3

3.04

CDCl3

3.19

CDCl3

3.40

CDCl3

4.06

DMSO-d6

1-Propynes

http://www.knowitall.com/handbook/hnmr/unsaturated_hydrocarbons/alkynes/alkynes.html（第 2／6 页）2005-10-1 21:49:45

The Sadtler Handbook of Proton NMR Spectra

δ

b

(ppm)

δ

a

-X

(ppm)

Solvent

2.23

3.29

CDCl3

2.31

3.99

2.39

3.97

2.41

3.83

-Br

CCl4

2.42

4.06

-Cl

CCl4

2.49

4.25

2.54

4.23

-O-CH3

CCl4 CDCl3

TFA

-OH

CDCl3

1-Butynes

δ

c

(ppm)

δ

b

(ppm)

δ

a

-X

(ppm)

1.40

Solvent CCl4

1.89

2.20

1.90

2.39

2.39

-C≡C-H

CCl4

1.96

2.38

2.67

-OH

CCl4

3.43 2.53

Polysol

2.55

2-Butynes (1,4-disubstituted)

http://www.knowitall.com/handbook/hnmr/unsaturated_hydrocarbons/alkynes/alkynes.html（第 3／6 页）2005-10-1 21:49:45

The Sadtler Handbook of Proton NMR Spectra

-X

δ

b

(ppm)

R5-

2.20

R4-

2.22

CH3-

2.23

R-

2.24

CH3-

2.26

δ

a

(ppm)

4.19

-Y

Solvent

-OH

CCl4

CDCl3

4.89 4.17

-OH

CCl4 CCl4

3.27

CDCl3

4.90

3.60

Polysol 3.60

3.68

CDCl3 4.61

Br-

3.98

3.98

-Br

CDCl3

Cl-

4.12

4.12

-Cl

CCl4

Cl-

4.12

CDCl3 4.68

Cl-

4.16

CDCl3 4.82

Cl-

Polysol

4.32 or 4.41

4.32

Polysol 4.79

4.65

CDCl3 4.65

Aromatic Protons The placement of various substituents on the triple bond opposite a phenyl group has only a slight effect upon the chemical shift ranges observed for the resulting complex, higher order bands. The fact that the lower field limit of these ranges is only about 0.2 ppm downfield from the chemical shift of unsubstituted benzene (7.37 ppm) indicates that the C≡C group has only a slight deshielding effect on the ortho aromatic hydrogens.

http://www.knowitall.com/handbook/hnmr/unsaturated_hydrocarbons/alkynes/alkynes.html（第 4／6 页）2005-10-1 21:49:45

The Sadtler Handbook of Proton NMR Spectra

Phenyl acetylenes

δ

a

-X

(ppm)

Solvent

7.00-7.65

-H

CDCl3

7.05-7.50

-R7

CCl4

7.10-7.50

-CH3

CDCl3

7.15-7.60

CDCl3

7.15-7.65

CDCl3

7.15-7.65

CCl4

7.20-7.65

CCl4

7.20-7.70

CDCl3

7.25-7.70

Polysol

Para substituted compounds

x

H-C≡C

δ

a

(ppm)

δ

b

para

(ppm)

7.42

6.85

7.43 or

7.30

Solvent

-O-CH3

CDCl3

-Br

CDCl3

Solubility and Solvent Effects

http://www.knowitall.com/handbook/hnmr/unsaturated_hydrocarbons/alkynes/alkynes.html（第 5／6 页）2005-10-1 21:49:45

The Sadtler Handbook of Proton NMR Spectra

The low molecular weight alkynes are readily soluble in the halogenated solvents normally used for the preparation of NMR solutions. It has been noted that the hydrogen bonded directly to the triple bond carbon is strongly deshielded in the presence of DMSO-d6 in comparison to CCl4 and CDCl3. For example, the acetylenic hydrogen of phenyl acetylene appears at about 3.0 ppm in CDCl3 solution but at 4.1 ppm in DMSO-d6.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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The Sadtler Handbook of Proton NMR Spectra

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Aromatic Hydrocarbons Monocyclics

Polycyclics

The aromatic protons of alkyl substituted benzene rings usually appear as a single broad peak near 7.1 ppm or a complex multiplet in the range from 6.9-7.5 ppm for highly branched chains such as the tert-butyl group. Aliphatic groups shield the ortho aromatic hydrogens by a factor of about 0.34 ppm, as evidenced by the aromatic resonance of mesitylene (1,3,5-trimethyl benzene) which appears at 6.69 ppm. Compound

(ppm)

Solvent

Benzene

7.37

CCI4

Toluene

7.04

CCI4

p-Xylene

7.07

CCI4

Mesitylene

6.69

CCI4

Aliphatic Protons

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The Sadtler Handbook of Proton NMR Spectra

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

-X

Solvent CCI4

2.29

CCI4 1.19

2.53

CDCI3 0.93

1.63

2.58

CCI4 (1.22)

2.83

CCI4 (1.32)

CDCI3 2.46

CDCI3 2.49

CCI4 1.37

3.03

CDCI3 1.30

2.77

The alkyl protons of aliphatic groups bonded to the naphthalene ring system resonate at lower field than those bonded to benzene, in addition, the groups bonded to carbons 1,4,5,8 resonate at lower field than similar groups situated at positions 2,3,6,7. The aromatic resonances of naphthalene ring systems generally appear as a complex, higher order series of multiplets in the range from 7.0-8.0 ppm.

Alpha-substituted toluenes

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The Sadtler Handbook of Proton NMR Spectra

δ

(ppm) b ca7.07

-X

Solvent

(ppm) a 2.53

-CH3

CCI4

ca 7.24

2.53

-C3

CDCI3

ca 6.94

2.91

ca7.14

3.33

ca 7.27

3.61

ca 7.27

3.62

-C≡N

CCI4

ca 7.22

3.64

-SH

CCI4

7.0-7.4

3.67

CDCI3

ca 7.29

3.85

CDCI3

ca 7.29

3.85

-NH2

ca7.59

4.27

-NH2 (salt)

D2O

ca 7.22

4.34

-Br

CCI4

7.07-7.5

4.38

-I

ca7.19

4.41

-OH

CCI4

ca 7.28

4.48

-Cl

CCI4

ca7.24

4.55

ca7.33

4.59

-n≡c

ca 7.29

4.59

-N=C=S

ca 7.44

4.83

ca 7.42

5.07

ca 7.27

5.24

δ

CDCI3

-CH=CH2

CCI4 CDCI3

CDCI3

CDCI3

CDCI3

CDCI3 CDCI3 CDCI3

Polysol

-F

CCI4

Aromatic Protons Para substituted toluenes (in increasing "meta" shift) http://www.knowitall.com/handbook/hnmr/unsaturated_hydrocarbons/aromatics/aromatics.html（第 3／6 页）2005-10-1 21:51:31

The Sadtler Handbook of Proton NMR Spectra

δ

c

(ppm)

δ

b

(ppm) δ

a

-X

(ppm)

CCI4

2.18

6.79

6.33

2..21

6.92

6.40

2.18

6.89

6.49

CCI4

2..21

7.01

6.59

CDCI3

2.22

6.93

6.62

2.20

-NH2

Solvent

-NH-CH3

CDCI3

-O-R12

CCI4

6.92

6.69

-OH

CDCI3

2.28

7.09

6.79

-O-CH3

CDCI3

2.23

7.00

6.81

-F

CCl4

2.28

7.01

6.82

CCI4

2.27

6.90

6.90

2.27

7.14

6.92

-CH3

DMSO-d6

CCl4

2.28

6.99

6.99

CCI4

2.28

7.01

7.01

-CH2-OH

CCI4

2.30

7.04

7.04

-CH2-CH3

CCI4

2.30

7.04

7.04

-CH2-NH2

CCI4

2.28

7.05

7.05

-S-CH3

CCI4

2.29

7.05

7.05

-CH2-C≡N

CCI4

2.34

7.07

7.07

CCI4

2.20

6.91

7.09

-SH

2.30

7.09

7.09

-CH2-CH2-NH2

CDC!3 CDC!3

2.31

7.10

7.10

-CH2-CH2-OH

CDCI3

-Cl

CCI4

2.29

6.98

7.12

2.29

7.00

7.12

CCI4

2.30

7.16

7.16

CDCI3

2.29

6.99

7.18

-CH2-Br

CC!4

2.28

7.02

7.18

-CH2-CI

CCI4

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The Sadtler Handbook of Proton NMR Spectra

2.33

7.19

7.19

CDCI3

2.30

7.07

7.21

CDC!3

2.25

6.95

7.30

-Br

CCI4

2.26

7.08

7.30

-Hg-CI

DMSO-d6

2.30

7.05

7.34

CDCI3

Para substituted toluenes (in increasing “meta”shift)

δ

c

(ppm)

δ

b

(ppm)

δ

a

para

(ppm)

Solvent

2.41

7.23

7.47

-C≡N

2.26

6.89

7.55

-I

2.35

7.20

7.55

CDCI3

2.36

7.22

7.55

CDCI3

2.32

7.24

7.58

DMSO-d6

2.36

7.35

7.58

D2O

2.33

7.21

7.59

DMSO-d6

2.30

7.21

7.61

2.39

7.22

7.65

CDCI3

2.32

7.09

7.69

CCI4

2.33

7.10

7.69

-SO2-OH (salt)

-N=S=O

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CCI4 CDCI3

DMSO-d6

CCI4

The Sadtler Handbook of Proton NMR Spectra

7.12

7.70

-SO2-OH (salt)

CDCI3

2.43

2.33

7.32

7.71

-SO2-O-CH3

CCl4

2.42

7.29

7.70

-SO2-O-R10

CCI4

7.31

7.76

CDCI3

2.43

7.37

7.79

CDCI3

2.39

7.22

7.83

CDCI3

2.41

2.46

7.37

7.84

7.25

7.84

CDCI3

2.29

7.26

7.88

D2O

2.30

7.15

7.89

CDCI3

2.39

2.50

-SO2-NH2

TFA

7.41

7.90

-SO2-F

CDCI3

2.49

7.41

7.90

-SO2-CI

CDCI3

2.49

7.43

7.92

TFA

2.44

7.24

7.96

CCI4

2.47

7.30

8.02

TFA

7.30

8.10

CDCI3

2.45

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Fluorinated Hydrocarbons Aliphatics

Fluorine containing compounds characteristically display coupling between the fluorine nuclei and nearby hydrogens. The multiplets which are produced are usually well resolved and the magnitude of the Fluorine-Hydrogen coupling constants is quite large in comparison to those produced by Hydrogen-Hydrogen and Phosphorus-Hydrogen coupling. Fluorine is a strong deshieider of aliphatic groups but has a moderately strong shielding effect upon the aromatic hydrogens that are ortho and para to it.

Aljphatic Protons

δ

b

(ppm)

δ

a

Compound

(ppm)

Solvent

3.72

4.37

CDCl3

1.8-1.9

4.3-4.4

CDCl3

Substituted Fluoromethanes

δ

a

(ppm)

-X

Solvent

4.75

D2O

4.88

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

5.02

TFA

5.07

D2O

5.11

CDCI3

5.24

CCI4

Coupling and Coupling Constants Aliphatic Protons J F-C-H J F-C-C-H J F2-C-C-H

=

46.7-51 .9 Hz

=

20.0-30.0 Hz

=

3.9-13.0 Hz

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Fluorinated Hydrocarbons Aromatics

Fluorine containing compounds characteristically display coupling between the fluorine nuclei and nearby hydrogens. The multiplets which are produced are usually well resolved and the magnitude of the Fluorine-Hydrogen coupling constants is quite large in comparison to those produced by Hydrogen-Hydrogen and Phosphorus-Hydrogen coupling. Fluorine is a strong deshieider of aliphatic groups but has a moderately strong shielding effect upon the aromatic hydrogens that are ortho and para to it.

Aromatic Protons Fluorine substituents on aromatic rings have a moderately strong shielding effect upon the ortho and para hydrogens and display coupling to the ortho, meta and para hydrogens.

Para-substituted fluorobenzenes

δ

b

(ppm)

δ

a

(ppm)

para-X

Solvent

6.81

7.00

-CH3

CCI4

6.89

7.09

-R

CCI4

6.90

7.12

-CH2-OH

CDCI3

6.90

7.15

-N=C=S

CCI4

6.90

7.23

-CH=CH2

CDCI3

6.91

7.19

-Cl

CDCl3

6.92

7.29

-CH2-Br

CCI4

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The Sadtler Handbook of Proton NMR Spectra

6.93

7.40

CCI4

6.99

7.19

-CH2-C≡N

CCI4

7.00

6.81

-O-CH3

CDCI3

7.11

7.99

CDCI3

7.15

8.01

CDCI3

7.17

7.66

-C≡N

CDCI3

7.20

8.20

-NO2

CDCI3

Para-substituted alpha,alpha,alpha-trifluorotoluenes

δ

b

(ppm)

δ

a

para-X

(ppm)

Solvent

7.46

6.91

-OH

CDCI3

7.49

7.60

-Br

CCI4

7.51

7.37

CDCI3

7.51

8.08

CDCI3

7.60

7.60

CDCI3

7.60

7.60

CDCI3

7.61

7.31

DMSO-d6

7.64

7.13

7.69

8.03

-F

CCI4 CCI4

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The Sadtler Handbook of Proton NMR Spectra

7.71

8.18

Polysol

7.73

8.20

CDCI3

7.80

7.80

-C≡N

CDCI3

Coupling and Coupling Constants Aromatic Protons JF-H (ortho) JF-H (meta) JF-H (para)

= 8.0-9.0 Hz = 5.0-6.0 Hz = 2.0-3.0 Hz

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Chlorinated Hydrocarbons Aliphatics

Because Chlorine does not possess a spin as Fluorine does, nor does it possess any exchangeable hydrogens, the identification of chlorine substituents via NMR must be based solely upon the observed chemical shifts. Fortunately, chlorine has a strong deshielding effect upon aliphatic hydrogens and thus the analysis of such materials is relatively straightforward. However, since it has only a very weak shielding/deshielding effect upon aromatic hydrogens, it becomes quite difficult to identify chlorine groups bonded to an aromatic ring without the use of alternate techniques.

Aliphatic Protons

δ

d

(ppm)

0.95

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

X

Solvent

3.05

(lit.)

1.33

3.47

(lit.)

1.05

1.77

3.45

CCl4

1.45

1.75

3.49

CCl4

(1.51)

4.11

CCl4

(1.61)

Substituted Chloromethanes

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CCl4

The Sadtler Handbook of Proton NMR Spectra

δ

a

-X

(ppm)

Solvent

4.05

CCI4

4.06

-C≡C-R

CCI4

4.11

-C≡N

CCI4

4.12

CDCI3

4.18

D2O

4.20

CDCI3

4.33

CDCI3

4.48

CCI4

4.50

CCI4

4.66

CDCI3

5.73

CCI4

2-Substituted Chloroethanes

δ

b

(ppm)

δ

a

-X

(ppm)

Solvent CCI4

3.61

3.00

3.61

3.61

-N=C=O

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

3.63

3.79

-OH

CDCI3

3.64

4.29

3.67

3.67

3.68

2.72

3.70

2.80

-C≡N

CCI4

3.70

3.56

-Br

CCI4

3.76

4.47

4.01

4.01

CCI4

-Cl

CCI4 CCI4

CDCI3

-SO2-CI

CCI4

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Chlorinated Hydrocarbons Aromatics

Because Chlorine does not possess a spin as Fluorine does, nor does it possess any exchangeable hydrogens, the identification of chlorine substituents via NMR must be based solely upon the ob-served chemical shifts. Fortunately, chlorine has a strong deshielding effect upon aliphatic hydrogens and thus the analysis of such materials is relatively straightforward. However, since it has only a very weak shielding/de-shielding effect upon aromatic hydrogens, it becomes quite difficult to identify chlorine groups bonded to an aromatic ring without the use of alternate techniques.

Aromatic Protons As noted previously, chlorine does not significantly alter the chemical shifts of aromatic hydrogens in comparison with the effects noted for other substituents. The NMR spectrum of chlorobenzene displays only a broad, single band at about 7.2 ppm.

para-substituted Chlorobenzenes

δ

(ppm) b 7.00

δ

(ppm) a 6.39

7.09

7.61

7.12

6.91

7.12

6.98

-X

Solvent

-NH-R

CDCI3

-I

CDCI3 CDCI3

-CH3

CCI4

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The Sadtler Handbook of Proton NMR Spectra

7.13

7.37

-Br

CCI4

7.19

6.91

-F

CDCI3

7.21

7.21

-CH=CH2

CCI4

7.22

6.85

-O-R

Polysol

7.23

7.23

-Cl

CCI4

7.27

7.02

-N=S=O

CDCl3

7.30

7.30

-CH2-CI

CCI4

7.31

7.80

CCI4

CDCI3 7.32

7.11

CCI4 7.36

7.84

7.40

7.81

CDCI3

7.45

7.45

PolysoI

7.46

8.02

CDCI3

7.55

7.97

DMSO

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Brominated Hydrocarbons Aliphatics

The Bromine nucleus is an intermediate deshielding group in relation to both aliphatic and aromatic hydrogens. It does not couple to nearby hydrogens and thus its presence in a molecule must be inferred from the observed chemical shifts.

Aliphatic Protons

δ

d

(ppm)

0.99

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent

1.66

3.34

CCl4

1.02

1.89

3.36

CCl4

1.43

1.82

3.39

CCl4

(1.08)

1.93

3.24

CCl4

3.15

CCl4

4.21

CCl4

(1.02)

(1.70)

(1.77)

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CCl4

The Sadtler Handbook of Proton NMR Spectra

Substituted Bromoethanes

δ

a

-X

(ppm)

Solvent

2.38

CCI4

3.21

Polysol

3.77

CCI4

3.83

-c≡c-h

CCI4

3.88

-CH=CH2

CCI4

3.91

D2O

3.92

CDCI3

3.98

CDCI3

-C≡C-R

4.38

CCI4

4.34

CCI4

4.40

CCI4

4.94

-Br

CCI4

5.18

-Cl

CCI4

2-Substituted Bromoethanes

δ

b

(ppm)

δ

a

(ppm)

3.40

3.65

3.41

2.04

-X -O-CH3

Solvent CCI4

CCI4

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The Sadtler Handbook of Proton NMR Spectra

3.45

3.85

3.51

2.36

3.53

2.97

-OH

CCI4 CCI4

-C≡N

3.56

CCI4 CDCI3

2.97

3.56

3.70

-Cl

CCI4

3.68

3.68

-Br

CDCI3

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Brominated Hydrocarbons Aromatics

The Bromine nucleus is an intermediate deshielding group in relation to both aliphatic and aromatic hydrogens. It does not couple to nearby hydrogens and thus its presence in a molecule must be inferred from the observed chemical shifts.

Aromatic Protons Bromine has a weakly deshielding effect upon the ortho aromatic hydrogens. The ortho hydrogens are deshielded to 7.41 ppm while the meta and para hydrogens appear as a complex higher order pattern centered to about 7.2 ppm.

para-substituted Bromobenzenes

δ

b

(ppm)

δ

a

(ppm)

-X

Solvent

7.18

7.50

-I

CDCI3

7.20

6.49

-NH-R

CDCI3

7.29

6.69

-O-CH3

CCI4

7.29

7.29

-Br

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

7.30

6.92

-CH3

CCI4

7.30

7.07

-SH

CDCI3

7.31

6.98

-R2

CDCI3

7.34

7.12

-CH=CH2

CCI4

7.37

7.13

-Cl

CCI4

7.39

7.11

-S-CH3

7.40

6.90

-F

7.45

7.62

-C≡N

7.49

7.60

-CF3

CDCI3 CCI4 CDCI3 CCI4 DMSO-d6

7.61 7.87

CDCI3

7.68 7.68

D2O

7.68 7.79

7.71

DMSO-d6 7.90

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Iodinated Compounds Aliphatics

Of the halogens, Iodine has the weakest deshielding effect upon aliphatic hydrogens, but the strongest deshielding effect on the ortho aromatic hydrogens. It is observed to have an unusually strong deshielding effect upon the hydrogens bonded to beta aliphatic carbon atoms.

Aliphatic Protons

(ppm)

δ d

0.99

(ppm)

δ

(ppm)

δ b

c

(ppm)

δ a

X

Solvent

2.20

CDCl 3

1.84

3.13

CCl 4

1.00

1.85

3.15

CCl 4

1.40

1.80

3.19

CCl 4

3.10

CCl 4

4.29

CCl 4

1.73 (1.01) (1.91)

Substituted lodomethanes

δ a

(ppm)

-X

Solvent

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The Sadtler Handbook of Proton NMR Spectra

3.55

-CF2-CF 3

CDCI

3

3.63

D2O

3.69

CCI 4

3.71

CDCI 3

3.80

-CH=CH 2

3.88

-I

CCI 4 CCI

4

3.98

TFA

4.38

CDCI

3

2-Substituted Iodoethanes

(ppm)

δ b

-X

(ppm)

δ

Solvent

a -CH2-CH2-I

CCI

3.17

1.94

3.19

3.08

3.28

3.81

3.30

3.09

3.29

2.29

-CH2-I

CDCI

3.70

3.70

-I

CCI

4

CDCI

-OH

3

CDCI CDCI

3

3

3

4

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Iodinated Compounds Aromatics

Of the halogens, Iodine has the weakest deshielding effect upon aliphatic hydrogens, but the strongest deshielding effect on the ortho aromatic hydrogens. It is observed to have an unusually strong deshielding effect upon the hydrogens bonded to beta aliphatic carbon atoms.

Aromatic Protons Of the four halogens, iodine has the strongest deshielding effect on aromatic hydrogens, pro-ducing a shift of the ortho hydrogens to 7.65 ppm.

δ b (ppm)

-X

δ a (ppm)

Solvent

7.40

7.40

-I

CDCI3

7.50

7.18

-Br

CDCI3

7.55

6.89

-CH3

CDCI3

7.55

7.95

-C≡N

Polyso I

7.58

6.78

-F

CDCI3

7.61

7.09

-Cl

CDCI3

7.61

7.88

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

7.69

7.99

CDCI3

7.71

7.90

DMSO-d6

7.78

7.78

Polysol

7.70

7.09

TFA

7.79

7.30

-CF3

CDCI3

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Primary Amines Aliphatics

The primary amines are often relatively easy to characterize due to the presence of the -NH2 group which appears as a broadened band at intermediate to high field (6.7-0.6 ppm). The primary amine group acts as a weak deshielding substituent on methyl, methylene and methine groups, but has a strong shielding effect upon the ortho and para aromatic hydrogens.

Aliphatic Protons

δ

c

(ppm)

0.91

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent

1.05

2.61

D2O

1.48

2.65

CCl4

(1.01)

3.04 D2O

(1.30)

Substituted Methylamines

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CDCl3

The Sadtler Handbook of Proton NMR Spectra

δ

a

(ppm)

-X

Solvent

2.52

CDCI3

3.12

D2O

3.30

CDCI3

-CH=CH2

3.58

D2O

3.76

D2O

3.85

CDCI3

CDCI3 3.86

2-Substituted Ethylamines

δ

c

(ppm)

1.55

1.19

δ

b

(ppm)

δ

a

-X

(ppm)

Solvent

2.65

1.48

-CH3

CCI4

2.99

2.49

-C≡N

D2O

3.18

2.53

2.86

2.59

-SH

D2O

2.60

2.60

-NH2

CCI4

D2O

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The Sadtler Handbook of Proton NMR Spectra

0.93

2.82

2.68

CCI4

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Primary Amines Aromatics

The primary amines are often relatively easy to characterize due to the presence of the -NH2 group which appears as a broadened band at intermediate to high field (6.7-0.6 ppm). The primary amine group acts as a weak deshielding substituent on methyl, methylene and methine groups, but has a strong shielding effect upon the ortho and para aromatic hydrogens.

Aromatic Protons The strong shielding effect of the primary amine group on the hydrogens of benzene is evident from the chemical shifts of the parent compound, aniline.

(ppm)

δ

δ

c 6.40

(ppm) b 7.00

δ

(ppm) a 6.59

Solvent CCI

4

Examples of para substituted Anilines.

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The Sadtler Handbook of Proton NMR Spectra

(ppm)

δ

-x

Solvent

6.34

(ppm) b 6.34

6.32

6.50

-S-CH

6.41

6.55

-R 2

CDCI 3

6.38

6.57

-SH

CDCI 3

6.59

6.59

CDCI

6.62

6.62

CDCI 3

6.49

6.65

-O-R 2

CDCI

6.68

6.72

-O-CH

CDCI

6.49

6.81

6.75

6.92

-CF 3

CDCI 3

6.60

7.02

-Cl

DMSO

6.62

7.09

6.57

7.21

6.55

7.26

DMSO

6.77

7.36

CDCI

6.37

7.37

6.70

7.39

6.67

7.60

6.79

7.77

CDCI 3

6.60

7.79

CDCI

δ

a

CDCI

3

3

3

CCI 4

3

3 3

DMSO-d 6

CDCI

-Br

-I

3

CDCI 3

3

CDCI 3 DMSO

-SO2-NH-R

DMSO-d

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3

6

The Sadtler Handbook of Proton NMR Spectra

Exchangeable Protons The NH2 Group range (ppm)

-Type

Solvent

0.66-1.52

Aliphatic-NH

1.72-1.78

Alicyclic- NH

3.30-6. 70

Aromatic- NH

2 2 2

CCI4, CDCI 3 CCI4, CDCI

3

CCI4, CDCI

3

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Secondary Amines Aliphatics

The secondary amines are similar in many respects to the primary amines except for the presence of one instead of two exchangeable hydrogens. A wider range of chemical shifts is observed because of the different types of groups bonded to the nitrogen nucleus. Phenyl substituted secondary amines display a stronger deshielding capability than their aliphatic counterparts. Like the primary and tertiary amines, the secondary type is capable of forming amine-acid salts upon the addition of acid to the sample solution resulting in shifts to lower field of about 0.8 ppm.

Aliphatic Protons Alkyl secondary amines

δ

d

(ppm)

δ

c

(ppm)

δ

(ppm) b 2.32

δ

a

(ppm)

Compound

D2O D2O

2.32 2.40

1.09 1.11 0.90

1.49

(0.88)

Solvent

1.49

CDCI3 D2O

2.60 2.65

1.23

CDCI3

2.58

0.85

CDCI3

2.31

0.79

CCI4

1.60

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The Sadtler Handbook of Proton NMR Spectra

2.76

D2O

(1.02) 2.88

0.67

CCI4

2.98

1.20

CDCI3

0.74

CDCI3

2.67

3.34

CCI4

3.03

3.23

CCI4

2.97

3.31

CCI4

3.54

3.19

CCI4

(1.00)

(1.01)

(1.00)

1.12

0.92 1.54

(1.12)

δ

a

(ppm)

-X

Solvent

2.07

CDCI3

2.48

CDCI3

2.60

-C4

CDCI3

2.60

-CH3

D2O

2.65

-CH3

CDCI3

3.13

3.22 3.38

D2O

-CH=CH2

CDCI3 CCI4

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The Sadtler Handbook of Proton NMR Spectra

δ

3.41

CDCI3

3.70

CCI4

3.68

D2O

b

(ppm)

-X

Solvent

2.58

(ppm) a 1.49

-CH3

CDCI3

2.61

2.61

-NH2

D2O

δ

2.62

CDCI3 0.80

δ

a

(ppm)

2.62

3.51

-OH

CCI4

2.70

3.41

-O-CH3

CCI4

2.76

2.90

-SH

CDCI3

2.76

2.76

-NH2

CDCI3

2.79

2.79

2.96

2.55

CDCI3

-C≡N

-X

Solvent

2.83

3.60

CCI4

-CH=CH2

3.71

3.77 3.78

CDCI3

CDCI3 CDCI3

-C≡N

CDCI3 CDCI3

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The Sadtler Handbook of Proton NMR Spectra

3.81

DMSO-d6

3.97

-c≡ch

CDCI3

4.22

4.40

-SO2-Na

DMSO

4.49

-SO2-R8

CDCI3

4.75

δ

CDCI3

b

CDCI3

(ppm) 2.97

(ppm) a 1.54

-CH3

3.00

2.75

-NH2

CCI4

3.22

3.78

-OH

CDCI3

δ

-X

Solvent CCI4

DMSO-d6

3.28 2.50 3.46

2.55

-C≡N

CDCI3 CDCI3

3.46 2.92

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Secondary Amines Aromatics

The secondary amines are similar in many respects to the primary amines except for the presence of one instead of two exchangeable hydrogens. A wider range of chemical shifts is observed because of the different types of groups bonded to the nitrogen nucleus. Phenyl sub-stituted secondary amines display a stronger deshielding capability than their aliphatic counterparts. Like the primary and tertiary amines, the secondary type is capable of forming amine-acid salts upon the addition of acid to the sample solution resulting in shifts to lower field of about 0.8 ppm.

Aromatic Protons

X-

δ

c

CH3-NH-

(ppm) 7.08

δ

(ppm) b 6.57

δ

7.20

(ppm) a 6.57

Solvent CCI4

6.83

CDCI3

6.83

Para-substituted secondary amines

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Solvent

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The Sadtler Handbook of Proton NMR Spectra

6.52

6.52

-NH-R

6.52

6.52

-OH

CDCI3 CDCI3

6.45

6.69

-O-CH3

Polysol

6.80

6.93

-R4

Polysol

6.45

6.96

-CH3

CDCI3 CDCI3

6.47 7.01

6.55

7.07

-Cl

DMSO-d6

6.83

7.10

-S-CH3

Polysol CDCI3

6.50 7.11

6.49

7.20

-Br

CDCI3

6.62

7.55

-SO2-NH2

Polysol

6.47

CDCI3 7.78

6.54

CDCI3 7.80

6.72

δ

c

(ppm)

7.84

6.81

(ppm) b 6.47

7.20

6.96

δ

-N=O

δ

Polysol

(ppm)

Solvent

-NH2

CDCI3

-O-CH3

CDCI3

a

7.45

7.45

-Cl

Polysol

7.08

7.77

-N=O

Polysol Acetone

7.09 8.05

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Tertiary Amines Aliphatics

The absence of an exchangeable hydrogen attached to the tertiary amine group makes this amine more difficult to characterize than either the primary or secondary amines. The large number of aliphatic and aromatic beta shift effects produce wider chemical shift ranges than nearly any other common functional group. A simple test for the presence of any amine including the tertiary variety is the addition of a few drops of weak mineral acid. The formation of the amine salt pro-duces significant shifts to lower field.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

X

Solvent

(2.14)

CCI4

(2.21)

CDCI3

(2.27)

CDCI3

(2.39)

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

0.90

(2.85)

CCI4

1.09

2.33

CDCI3

0.98

2.42

CCl4

1.10

3.27

CCI4

0.88

1.36

2.31

CCI4

1.25

1.35

2.31

CCI4

(0.97)

3.02

CCI4

Substituted Trimethylamines

δ

a

(ppm) 2.33

-X

Solvent

-CH3

CDCI3 CDCI3

2.72

2.93

-CH=CH2

CDCI3

3.07

CDCI3

3.07

CCI4

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The Sadtler Handbook of Proton NMR Spectra

3.20

CDCI3

3.29

CDCI3

3.33

CCI4

3.42

CDCI3

3.49

-C≡N

3.69

δ

a

(ppm)

CDCI3 CDCI3

-X

Solvent

3.30

-CH3

CCI4

3.84

-CH=CH2

CCI4

3.95

-C≡C-R

CDCI3

3.99

DMSO-d6

4.41

CCI4

4.70

CDCI3

4.89

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

δ

b

(ppm)

δ

a

(ppm)

-X

2.41

Solvent CCI4

2.41

D2O

2.81 2.45

2.63

2.63

-SH

CDCI3

2.41

2.69

-NH2

D2O

2.70

CDCI3 2.70

CDCI3

2.70 2.70

2.70

CCI4 4.15

δ

b

(ppm)

δ

a

(ppm)

-X

Solvent

3.13

1.59

-CH3

CCI4

3.21

3.50

-OH

CCI4

3.60

DMSO-d6 2.49

3.61

3.61

-Cl

Polysol

3.65

2.50

-C≡N

CDCI3

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Tertiary Amines Aromatics

The absence of an exchangeable hydrogen attached to the tertiary amine group makes this amine more difficult to characterize than either the primary or secondary amines. The large number of aliphatic and aromatic beta shift effects produce wider chemical shift ranges than nearly any other common functional group. A simple test for the presence of any amine including the tertiary variety is the addition of a few drops of weak mineral acid. The formation of the amine salt pro-duces significant shifts to lower field.

Aromatic Protons Phenyl Amines

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Solvent

6.57

7.10

6.57

CCI4

6.56

7.07

6.48

CCI4

6.52

7.02

6.48

CCI4

6.86

7.23

6.82

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

7.05-7.60

CDCI3

6.80-7.40

CDCI3

Para substituted aromatics

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Solvent

6.62

6.62

-NH2

CDCI3

6.79

6.79

-O-CH3

CDCI3

6.77

7.00

CDCI3

6.62

7.01

CDCI3

6.53

7.25

6.63

7.33

CDCI3

6.63

7.63

CDCI3

6.60

7.70

6.65

7.73

CDCI3

6.61

7.73

CDCI3

6.60

7.80

CDCI3

6.71

7.95

CDCI3

-Br

-N=O

CDCI3

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

δ

c

(ppm)

6.69

7.99

CDCI3

6.58

8.08

CDCI3

δ

b

(ppm)

δ

a

(ppm)

Solvent

6.59

6.59

-NH2

CDCI3

6.76

6.76

-O-CH3

CDCI3

6.59

7.01

-CH3

CDCI3

6.70

7.15

-Cl

DMSO-d6

6.48

7.20

-Br

CDCI3

6.58

7.35

-C≡N

CDCI3

6.57

7.56

CDCI3

6.62

7.75

CDCI3

6.78

7.77

CDCI3

6.65

7.79

-N=O

CDCI3

6.71

7.84

-N=N-O

CDCI3

6.70

8.02

CDCI3

6.59

8.08

CDCI3

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Pyridines

The proton NMR spectra of the pyridines produce characteristic patterns over a wide range of chemical shifts. The chemical shifts of the individual ring protons and the coupling constants with other pro-tons on the ring vary with their position relative to the pyridine nitrogen atom. The characteristic low field chemical shifts observed for the hydrogens at positions 2 and 6 (adjacent to the ring nitro-gen atom) are a distinct aid in the identification of the NMR spectra of this class of compounds.

Aromatic Protons

δ

c

(ppm)

δ

7.55

b

(ppm)

δ

7.14

a

(ppm)

Compound

Solvent

Pyridine

CCl4

8.51

2-Substituted Pyridines

δ

e

(ppm) 7.93

(ppm) d 6.48

8.07

6.45

7.36

6.45

-NH-R

CDCI3

8.14

6.83

7.52

6.68

-O-CH3

CCI4

7.14

7.77

6.89

-F

CCI4

8.46

6.98

7.48

7.05

-CH2-CH3

CCI4

8.37

7.20

7.68

7.29

-Cl

CCI4

8.18

δ

δ

(ppm) c 7.22

δ

(ppm) b 6.36

-NH2

δ

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a

(ppm)

Solvent CDCI3

The Sadtler Handbook of Proton NMR Spectra

8.27

7.20

7.48

7.38

-Br

CCI4

8.76

7.60

7.75

7.89

-C≡N

CCI4

8.71

7.39

7.81

7.90

CCI4

8.78

7.58

7.91

7.91

CCI4

8.70

7.46

7.81

8.03

CCI4

8.57

7.41

7.83

8.21

8.27

7.03

7.70

8.27

8.67

7.25

7.77

8.42

CDCI3

CDCI3

CDCI3

3-Substituted Pyridines

δ

d

(ppm) 7.92

6.95

6.95

-X

(ppm) a 8.04

8.32

7.01

7.35

-X

8.33

7.10

7.42

-X

8.41

7.15

7.59

8.50

7.21

8.48

7.10

δ

c

(ppm)

δ

b

(ppm)

-X

δ

b

(ppm)

8.03

δ

a

CDCI3

8.36

-CH3

CCI4

8.38

-CH2-CH3

CCI4

-X

8.52

-Cl

CCI4

7.62

-X

8.53

7.74

-X

8.66

X

(ppm)

6.50

Solvent

-NH2

4-Substituted Pyridines

δ

-X

-NH2

Solvent Polysol

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CDCI3

-Br

CCI4

The Sadtler Handbook of Proton NMR Spectra

8.25

6.50

CDCI3

8.37

6.98

8.41

7.02

- CH2CH3

CCI4

8.51

7.26

-CH2-NH-CH3

CDCI3

8.63

7.40

CDCI3

8.71

7.51

CDCI3

8.82

7.64

CCI4

-CH3

CCI4

Coupling and Coupling Constants The spin-spin couplings of the pyridines is limited to those between hydrogens on the ring. The protons at positions 2 and 6 often display an observable degree of broadening due to the adjacent nitrogen nucleus. The coupling constants observed for the pyridines are unusual in that long range "para" couplings are observed through five bonds and that the two "ortho" couplings J2-3 and J3-4 are different in magnitude.

J J J J J

2-3 = 4-7 Hz 3-4 = 7-9 Hz 2-4 = 1-3 Hz 2-5 = 0.1-1.1 Hz 3-5 = 1.1-2.5 Hz

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Quaternary Ammonium Compounds

The quaternary ammonium compounds display low field chemical shifts for the aliphatic groups bonded to the nitrogen atom. The groups often show a certain degree of broadening, possibly due to unresolved coupling to the nitrogen nucleus. The compounds are more soluble in D2Oand DMSO-d6 than the corresponding tertiary amines. Relatively large ranges of chemical shifts are observed for similar groups on different environments. No consistant correlation with solvent, concentration or anion has been observed to explain these variations.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ a (ppm)

X

Solvent D2O

(2.99)

D2O (3.15)

D2O (3.21)

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The Sadtler Handbook of Proton NMR Spectra

Polysol (3.30)

CDCI3 (3.40)

CDCI3 (3.48)

D2O (1.26

3.24)

Polysol (1.30

3.40)

D2O (1.28

3.95)

D2O (0.92

1.70

3.16)

CDCI3 (1.08

1.92

3.35)

CDCI3 (1.08

1.81

3.39)

TFA

(1.02 1.45

1.70

3.22)

CDCI3

(1.03 1.45

1.60

3.41)

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The Sadtler Handbook of Proton NMR Spectra

(1.01

CDCI3 1.43

1.65

3.42)

Substituted Methyl Ammonium Compounds

δ

b

(ppm)

δ

a

-X

(ppm)

Solvent

(3.29)

3.48

-C3

I¯

(3.12)

3.95

-CH=CH2

Br¯

Polysol

D2O

(3.31)

D2O 4.09

Cl¯

4.22

Cl¯

4.53

Br¯

D2O

(3.30)

D2O

(3.15)

2-Substituted Ethyl Ammonium Compounds

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Solvent

-X

3.29

3.55

3.31

3.19

3.80

3.80

-Br

3.18

3.49

4.02

-OH

3.26

3.81

4.03

-Cl

I¯

Br¯

Poly so I

D2O D2O

Cl¯

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D2O

The Sadtler Handbook of Proton NMR Spectra

3.26

3.79

4.55

D2O Br¯

3.30

3.80

D2O

4.57 I¯

Olefinic Protons The trimethylammonium group has an unusually strong and long range deshielding effect on the two terminal olefinic protons of allyl groups. In the spectrum of Allyltrimethylammonium Bro-mide, all three olefinic protons resonate in the chemical shift range from 5.4 to 6.2 ppm as a higher order ABC pattern. Normally, the terminal olefinic protons of allyl groups resonate at about 5.1 ppm as the AB portion of an ABX system.

Aromatic Protons The chemical shifts of the quaternary ammonium aromatic compounds are dependent to a signi-ficant degree upon the solvent employed and/or the amount of water present in the sample solution. As an example, when benzyl trimethyl ammonium chloride was examined in CDCI3 the ortho protons are strongly deshielded in relation to the meta and para hydrogens. In Polysol and DMSO-d6 solution, all five protons resonate as a single complex band. In D2O solution, the five protons appear as a single sharp peak at about 7.5 ppm. A somewhat similar case of solvent deshielding is noted in which the aromatic protons of the compound examined in CDCI3 solution resonate at lower field than those of a similar compound in D2O.

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Hydrazines

The chemical shifts produced by Hydrazine substituents are similar to those observed for the corresponding primary, secondary or tertiary amines. The hydrazine protons, on the average, resonate midway between the high field resonance of the aliphatic amines and the low field resonance of the aromatic amine protons. The presence of a Hydrazine linkage in a molecule could be detected most easily if the integration ratio indicated either more hydrocarbon groups or more exchangeable hydrogens than a simple amine group could accommodate. As with the amines, the Hydrazine group undergoes salt formation upon the addition of acid to the sample solution producing a shift to lower field for the Hydrazine protons and the protons of aliphatic or aromatic groups bonded to it.

Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

(2.35)

2.61

3.36

δ a (ppm)

Solvent

3.00

CCl4

3.36

CH3-NH-NH2

CCl4

The series of substituted ethanols presented below illustrates the comparative deshielding effect of the amines and hydrazines.

δ

b

(ppm) 3.47

δ a (ppm) 2.38

-X

Solvent CCI4

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The Sadtler Handbook of Proton NMR Spectra

3.69

2.69

-NH-CH3

3.54

2.73

-NH2

3.74

2.93

-NH-NH2

D2O CDCI3 D2O

Aromatic Protons

δ c (ppm)

δ

b

(ppm))

δ

a

(ppm)

6.52

7.00

6.52

6.60

7.07

6.76

-X -NH-NH2

Solvent CCI4

DMSO-d6

CDCI3 1.2-2.1

1.2-2.1

3.72

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Amine Salts

The reaction of mineral acids with primary, secondary and tertiary amines to form amine salts not only makes the compounds more soluble in polar solvents such as D2O, but increases the deshielding effect of the amine group on both aliphatic and aromatic hydrogens. The exchangeable hydrogens attached to the nitrogen nucleus normally resonate at a lower field than the corresponding hydrogens of the free amine. The amine salts can be neutralized by the addition of a few drops of a sodium bicarbonate solution to the sample. The amine salt is thus converted to the free base form with an attendant shift to higher field for proton containing groups bonded to the nitrogen atom.

Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

δ a (ppm)

Compound

2.62

(2.76)

(2.94)

Solvent D2O D2O

D2O

CDCI3 (1.45

3.03)

1.30

3.08

D2O

1.22

3.10

D2O

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D2O (1.30

3.10)

1.41

3.31

1.50

3.37

(1.29)

3.33

0.93

1.76

2.91

1.11

1.99

3.39

D2O

CDCI3

DMSO-d6

CDCI3 TFA

2-Substituted Ethylamine salts

δ

b

(ppm) 2.75 3.19

3.22

δ

a

(ppm)

1.64

-X

Solvent

-CH 3

DMSO-d6 D2O

2.22 2.85

-SH

D2O

3.36

D2O 2.85

3.27 3.42

3.75 3.55

3.40

-SO3H

D2O D2O

3.42 3.55

-Br

D2O D2O

3.55

3.18

3.85

-OH

D2O

3.48

4.01

-Cl

D2O

Substituted Methylamine salts

δ

a

(ppm)

-X

Solvent

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2.90

D2O

3.08

-CH3

D2O

3.09

-R3

CDCI3

3.60

-CH=CH2

Polysol

3.88

D2O

3.99

D2O

4.19

-C≡N

D2O

4.27

D2O

4.29

D2O

5.05

TFA

Aromatic Protons As a substituent on an aromatic ring, the amine salt group has an unusually uniform effect on the chemical shifts of the ortho, meta and para hydrogens. The series of aniline salts presented indicate the minimal effect that the type of acid involved, the solvent employed and the degree of amine substitution have on the chemical shift of the phenyl protons. The aromatic resonance for all of these aniline salts appears as a relatively sharp peak in the narrow chemical shift range from 7.50-7.55 ppm. δ (ppm)

Compound

Solvent

7.51

D2O

7.51

TFA

7.54

D2O

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7.54

DMSO-d6

7.55

D2O

Para substituted aniline salts

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Solvent

7.19

6.67

-O-R2

D2O

7.22

6.88

-OH

DMSO-d6

7.44

7.09

-O-CH3

D2O

7.33

7.33

-CH3

TFA

7.67

7.39

-Br

D2O

7.46

7.46

7.56

7.56

7.78

7.78

7.78

7.78

D2O

7.79

7.79

D2O

7.79

7.79

D2O

7.20

7.90

DMSO-d6

D2O

-Cl

Exchangeable Protons

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D2O D2O

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The chemical shifts of the exchangeable protons of the amine salts are especially unreliable. Because they are sensitive to sample concentration, the presence of H2O and structural differences in-volving substitution of the amine nitrogen nucleus, they are observed to resonate over a wide range of chemical shifts from 5.0 to 12.0 ppm. The corresponding chemical shift range for primary and secondary amines (not salts) is about 1.5 ppm (1.0-2.5 ppm). There does not appear to be any relationship between the type of acid used to form the salt and the chemical shift of the resultant exchangeable hydrogens.

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Ylidene Compounds

The benzylidene and cinnamylidene compounds correspond to oxime-like structures in which the -OH has been replaced by a hydrocarbon group. Because both sides of the CH=N group are sub-stituted by bulky hydrocarbon groups, syn-/anti- isomerism is not ordinarily observed in the NMR spectra. It is assumed that the compounds exist primarily in the anti- form (substituents on op-posite sides of the CH=N bond). The spectra characteristically display a single band at relatively low field (7.9-8.4 ppm). For the benzylidene compounds the band is a sharp singlet, for the cinnamylide compounds the band ap-pears as a sharp triplet or doublet of doublets.

Aliphatic Protons

δ

c

(ppm)

0.95

δ

b

(ppm)

1.69

δ

a

(ppm)

X

Solvent

3.49

CDCI3

3.48

CCI4

3.41

CDCI3

(1.23)

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X

δ

a

Y

(ppm)

7.95

-R

8.07

Solvent CDCI3

CDCI3

8.11

-CH3

CDCI3

8.13

-R3

CDCI3

8.15

CDCI3

8.18

CCI4

8.40

CDCI3

Coupling and Coupling Constants Aliphatic groups are observed to couple weakly across the—CH=N— bond. The couplings vary from a slight broadening effect (J less than 0.8 Hz) to clear 5 Hz multiplets in the case of the cinnamyli-dene compounds. J CH3-N=CH= =2 Hz J J

CH2-N=CH- = 0-1 Hz C=CH-CH=N- = 4-5 Hz

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Oximes

The oximes of aldehydes which contain an HO—N=CH— group are easily identified by the pre-sence of two clear n+1 multiplets in the range from 6.4 to 7.5 ppm arising from the syn and (anti) forms of the CH=N proton. The oximes of ketones (HO—N=C(R)—R) do not possess such a pro-ton and are thus more difficult to characterize. Both forms possess an N—OH hydroxyl group which usually appears as a rather broad resonance band in the chemical shift range from 7.8 to 9.6 ppm. The deshielding effect of the oxime group is similar to that of the C=C group of the alkenes.

Aliphatic Protons

δ

b

(ppm)

δ

a

X

(ppm)

Solvent

1.88

7.98

-H

CDCI3

1.88

9.08

-R3

CDCI3

1.89

9.55

-R2

CDCI3

2.25

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

δ

c

(ppm)

0.91

δ

b

(ppm)

δ

b

(ppm)

δ

a

X

(ppm)

Solvent

1.09

2.22

CDCI3

1.56

2.25

CDCI3

(1.10)

2.44

CCI4

(1.08)

3.19

CCI4

δ

a

(ppm)

-X

9.80

6.44

8.45

6.44

9.80

6.71

-R6

CDCI3

7.98

6.83

-CH3

CDCI3

8.45

7.23

7.98

7.45

-CH3

CDCI3

7.82

-CH=N-OH

DMSO

9.91

8.21

7.52

9.42

-R6

Solvent CDCI3 CCI4

CCI4

Aromatic Protons

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CDCI3

CDCI3

The Sadtler Handbook of Proton NMR Spectra

δ

b

(ppm)

δ

a

(ppm)

X

Solvent

-CH=N-OH

CDCl3

7.1-7.4

7.52

7.2-7.6

7.78

CDCl3

7.2-7.6

7.88

CDCl3

Coupling and Coupling Constants Coupling between the CH=N proton and adjacent aliphatic groups is similar in magnitude to that of the corresponding coupling of the alkenes, JCH-CH=N = 6.0-7.0 Hz.

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Hydrazones

The hydrazones which are primarily used as derivatives for the characterization of ketones and aldehydes produce rather wide ranges of chemical shifts for the —CH=N— proton and for the various types of NH hydrogens. Both groups are quite sensitive to the substituent and its position on adjacent aromatic rings, various nitro-phenyl hydrazones being a common variety.

Aliphatic Protons

(ppm)

δ

(ppm)

δ

(ppm)

δ

c

b

a

0.96

1.51

2.12

Range (ppm)

Group

3.35-3.42

CH3-

5.37-6.53

NH2-

6.90-10.98

-NH-

X

Solvent

CCl 4

Structure

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7.27-8.06

-N=CH-

Aromatic Protons The aromatic hydrogens of phenyl groups bonded to the hydrazone group cover a relatively wide range of chemical shifts. The carbon side of the group is a moderately strong deshielding group in relation to the ortho protons while the amine side of the group shields the para hydrogen rather strangely. Because two different rings are often present the aromatic patterns can become quite complex.

(ppm)

δ c

(ppm)

δ b

(ppm)

δ a

Solvent

6.73

6.9-7.4

6.9-7.4

Acetone

6.9-7.4

6.9-7.4

7.60

Acetone

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Azines

The symmetrical structure of the azine group generally produces less complex spectra than groups such as the Hydrazones. Azine derivatives are usually produced from only one type of aromatic aldehyde so that the two protons of the azine group are equivalent. In com-pounds synthesized utilizing two different aromatic aldehydes, the azine protons will appear as separate resonances at low field. The overall range of chemical shifts for some azines was found to be:

δ

a

Compound

(ppm)

Solvent

8.51-9.01 ppm

CDCI3, Polysol

As observed for the Hydrazones, the -CH=N- group deshields the ortho aromatic hydrogens which resonate at about 7.78 ppm for a phenyl group.

Aromatic Protons

δ

b

(ppm)

δ

7.1-7.5

a

(ppm)

-X

7.78

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Solvent

CCl4

The Sadtler Handbook of Proton NMR Spectra

δ

b

(ppm)

δ

a

(ppm)

para

Solvent

7.78

6.95

-O-CH3

CDCl3

7.72

7.22

-CH3

CDCl3

Coupling and Coupling Constants The band arising from the azine protons usually appears slightly broadened indicating the possibility that a very small coupling may exist between it and the ortho aromatic hydrogens. If the coupling in fact does exist it is quite small, less than 0.8 Hz. Derivatives of cinnamaldehyde which result in an olefinic bond adjacent to the azine linkage display clear coupling between the azine protons and the olefinic hydrogens. Although this proton appears as a triplet, equal coupling across the C—C double bond is unlikely and the triplet probably represents a higher order multiplet of the ABX type. A coupling constant of about 5 Hz for the protons of C=CH-CH=N- appears reasonable.

Solvent Effects The simple aromatic azines are soluble in the halogenated hydrocarbons such as CCl4 and CDCI3. More polar solvents such as Polysol or DMSOd6 may be required depending upon the type of substituents on the aromatic rings. There does not appear to be any special chemical shift relation-ship between the azine protons and the solvent employed.

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Amidines

The most characteristic feature of the Amidines is the appearance of the -CH=N- proton as a relatively sharp singlet near 7.3 ppm. The chemical shifts and multiplets observed in the spectra can appear in a large number of possible combinations of aliphatic and aromatic groups. The methyl resonance of the dimethyl formamidines is fairly constant in chemical shift resonating in the range from 2.8 to 3.0 ppm. As a substituent, the nitrogen nucleus on the N=CH side of the linkage is observed to be a relatively strong shielding group in its effect on the ortho aromatic hydrogens. Exchangeable –NH- protons, when present can appear as very broad bands at low field or as relatively sharp bands at much higher field. Because the CH=N proton is isolated from other proton groups by the two nitrogen atoms, it does not display any clear couplings.

Aromatic Protons

δ b (ppm)

δ

a

(ppm)

Compound

Solvent

6.8-7.3

6.75

CCI4

6.9-7.3

6.80

CCI4

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The Sadtler Handbook of Proton NMR Spectra

6.9-7.5

6.85

DMSO-d6

7.2-7.5

7.91

DMSO-d6

Some spectra display extremely similar aromatic patterns for these sym-metrically substituted amidine groups. It can be inferred that one is observing an "averaged" structure via resonance in which the double bond is shared by the nitrogen atoms endowing them with identical shielding/ deshielding effects. This phenomenon is not observed in the unsymmetrical structures of this type.

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Hydroxamic Acids

Although traditionally structured as N-Hydroxyamides, infrared spectral evidence indicates that the Hydroxamic Acids possess a Hydroxyoxime-like structure of the type R-C(OH)=N-OH. The group has a weakly deshielding effect on adjacent hydrocarbon group protons but a strongly deshielding effect on the ortho aromatic hydrogens. The two OH protons are usually in exchange and resonate as a single, rather broad band at low field (8-11 ppm). The Hydroxamic acids are generally more soluble in DMSO-d6, polysol and trifluoroacetic acid than in deuterochloroform or carbon tetrachloride.

Aliphatic Protons

-X

δ R4-

b

(ppm) 2.20

δ

a

(ppm)

ca. 8.60

Solvent CDCI3

R15-

2.51

TFA

(R)2-C=CH-

2.81

8.1-9.6

Polysol

C6-O-

4.04

ca. 8.54

Polysol

Aromatic Protons

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The Sadtler Handbook of Proton NMR Spectra

δ

c

(ppm)

δ

b

(ppm)

7.2-7.6

δ

c

(ppm) -NO2

7.80

δ

b

(ppm) 8.29

δ

a

-X

(ppm)

Solvent

~10.2

δ

Polysol

a

(ppm)

-X

8.07

Solvent Polysol

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AZO Compounds

The AZO linkage between aromatic rings acts as a strong deshielding group on the ortho hydrogens. Due to the bulk of the aromatic rings, these compounds most likely exist only in the anti- form. The only major solvent effect upon the deshielding ability of the AZO linkage is observed when these compounds are scanned as solutions in Trifluoroacetic acid. For these solutions, the hydrogens ortho to the AZO linkage are deshielded by an additional 0.3-0.4 ppm. The AZO compounds are readily soluble in CDCI3, depending upon the nature of the other substituents present in the compound.

Aromatic Protons

δ b (ppm) 7.4-7.8

δ

a

(ppm)

7.96

X

Solvent

CDCl3

Para substituted Azobenzenes

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The Sadtler Handbook of Proton NMR Spectra

δ

b

(ppm)

δ

a

para

(ppm)

-NH-CH3

Solvent

7.78

6.47

CDCI3

7.83

6.63

7.80

7.00

-OH

DMSO-d6

7.90

7.00

-O-CH3

CDCI3

7.82

7.11

-F

CDCI3

7.87

7.20

7.80

7.30

-CH3

CDCI3

7.92

7.30

-R2

CDCI3

7.73

7.31

-S-CH3

CDCI3

7.81

7.40

-Cl

CDCI3

7.70

7.70

7.88

7.88

7.79

7.98

CDCI3

8.01

8.01

DMSO

8.08

8.17

7.90

8.21

CDCI3

7.98

8.24

DMSO

7.92

8.32

CDCI3

CDCI3

CDCI3

Poly so I

-SO3Na

-SO2-CI

DMSO

CDCI3

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Isocyanates

The isocyanate group has a moderate deshielding effect on aliphatic protons but a slight shielding effect on the ortho aromatic hydrogens.

Aliphatic Protons

δ c

(ppm)

(ppm)

δ b

δ a

X

(ppm)

Solvent

3.01

CDCI

3

0.98

1.61

3.29

CDCI 3

(1.1-

1.9)

3.24

CCI 4

( 1.1-

1.9)

3.29

CH3-(CH2)10-CH2-N=C=O

Aromatic Protons Phenyl Isocyanates

(ppm)

δ b

(ppm)

δ a

para

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Solvent

CCI 4

The Sadtler Handbook of Proton NMR Spectra

7.02

6.81

6.98

7.07

7.10

7.10

-O-CH

3

CDCl 3 Polysol

-O-CF 3

CCl 4

Solubility and Solvent Effects The Isocyanates are readily soluble in the halogenated solvents normally used to prepare NMR solutions. The aromatic Isocyanates may require more polar solvents such as D2O or DMSO-d depending on the character of the other substituents on the phenylisocyanate ring. 6

Characterization Because the Isocyanate group is neither strongly shielding nor deshielding, possesses no exchangeable protons and displays no coupling to nearby protons, it is a very difficult functional group to identify based only on NMR data. Fortunately, this group is readily identified via its infrared absorption bands.

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Carbodiimides

Although relatively few compounds containing the carbodiimide linkage are available, the indication is that the chemical shifts of both the aliphatic and aromatic groups bonded to it are similar to those of the isocyanates (-N=C=O), the benzylidenes (N=CH—Ar) and the isothiocyanates (-N=C=S).

Aliphatic Protons

δ

b

(ppm)

δ

1.22

a

X

(ppm)

Solvent

3.53

CDCl3

CDCl3

0.98

Alicyclic Protons Dicyclohexylcarbodiimide

(ppm)

δ b

0.9-2.2

(ppm)

δ a

3.17

X

Solvent

CDCl3

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The Sadtler Handbook of Proton NMR Spectra

Aromatic Protons The Carbodiimide group is a weakly shielding group on the ortho aromatic hydrogens similar to a methyl substituent. Its presence in a molecule would be dif-ficult to detect without the corresponding infrared data.

Syn-/Anti- Isomerism Although both syn- and anti-forms can exist, most of the spectra examined do not display the duplication of resonance bands expected in the spectra of such a mixture. It is assumed that the groups most often exist in the anti- form. One possible exception is noted when one com-pares the aromatic trityl resonance bands (a single broad band near 7.28 ppm) and the corresponding band of a complex, higher order series of multiplets in the range from 6.8 to 7.3 ppm.

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Isothiocyanates

The esters of Isothiocyanic Acid (R—N=C=S) possess chemical shifts similar to those of the other -N=C= groups. The protons of adjacent aliphatic groups resonate in the range from 3.3 to 4.6 ppm. The —N=C=S group exerts a weakly deshielding effect on the ortho aromatic protons.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

1.37 0.99

(1.2-2.1)

X

Solvent

3.30

CH3-N=C=S

CDCl3

3.55

CH3-CH2-N=C=S

CDCl3

CH3-(CH2)2-CH2-N=C=S

CCl4

(CH3)3-C-N=C=S

CCl4

a

(ppm)

(1.45)

Phenethyl Isothiocyanate

δ

b

(ppm)

3.48

δ

a

(ppm)

X

2.79

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Solvent

CCl4

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Substituted Methylisothiocyanates S=C=N=CH2-X δ

a

Compound

(ppm)

Solvent

3.48

CDCI3

4.15

-CH=CH2

CCI4 CDCI3

4.59

Aromatic Protons Phenyl Isothiocyanate

δ

a

Compound

(ppm)

Solvent

6.95-7.50

CCl

4

Para-substituted aromatics

δ

b

(ppm)

δ

a

(ppm)

para

Solvent

7.15

6.98

-F

CCI4

7.10

7.25

-Cl

CDCI3

7.08

7.45

-Br

CDCI3

7.25

8.02

7.38

8.28

CDCI3

CDCI3

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Nitriles Aliphatics

A large amount of chemical shift data is available for this commercially important group of compounds. The nitrile group is a weak deshielder of aliphatic and aromatic protons, similar to several other unsaturated carbon-carbon and carbon-nitrogen functional groups. Fortunately, the nitrile group is easily characterized by its infrared absorption band allowing the NMR analyst to concen-trate his energies on the proton groups in the molecules which are less easily defined by the infrared data.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

1.07

0.97

δ

b

(ppm)

a

(ppm)

X

Solvent

1.94

CH3-C≡N

CCI4

1.25

2.34

CH3-CH2-C≡N

CCI4

1.67

2.27

CH3-CH2-CH2-C≡N

CCI4

(1.30)

2.69

(CH3)2-CH-C≡N

CCI4

2.30

CH3-(CH2)2-CH2-C≡N

CCI4

2.21

(CH3)2-CH-CH2-C≡N

CCI4

(CH3)3-C-C≡N

CCI4

(1.2-1.9) (1.08)

δ

1.97 (1.39)

2-Substituted Nitriloethanes

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δ

b

(ppm) 2.27

δ

a

X

(ppm)

1.67

Solvent

-CH3

CCI4 CCI4

2.62 2.62

CDCI3

2.36 2.73

2.78

2.78

-C≡N

CDCI3

2.55

2.96

-NH-(CH2)2-C≡N

CDCI3

2.49

2.99

-NH2

CDCI3

2.83

3.20

-NH2 (TFA salt)

D2O

2.97

3.53

-Br

CCI4

2.80

3.70

-Cl

CCI4

2.67

3.73

-O-(CH2)2-C≡N

CDCI3

2.61

3.85

-OH

CDCI3

Substituted Nitrilomethanes

δ

a

-X

(ppm) 2.34

-CH3

CCI4 CCI4

2.48

3.10

Solvent

-CH=CH2

CCI4

3.50

CDCI3

3.62

CCI4

3.79

DMSO-d6

4.21

-C≡N

DMSO-d6

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Nitriles Olefinics

A large amount of chemical shift data is available for this commercially important group of compounds. The nitrile group is a weak deshielder of aliphatic and aromatic protons, similar to several other unsaturated carbon-carbon and carbon-nitrogen functional groups. Fortunately, the nitrile group is easily characterized by its infrared absorption band allowing the NMR analyst to concen-trate his energies on the proton groups in the molecules which are less easily defined by the infrared data.

Olefinic Protons Although the nitrile group deshields all of the vinyl protons, it has an abnormally strong deshielding effect upon the cis olefinic hydrogen.

Acrylonitrile

cis (ppm)

trans (ppm)

geminal (ppm)

-X

Solvent

6.20

5.95

5.60

-C≡N

CCl

Methacrylonitrile

cis (ppm)

trans (ppm)

-X

Solvent

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4

The Sadtler Handbook of Proton NMR Spectra

ca 5.79

1.98

-C≡N

CCl 4

cis (ppm)

trans (ppm)

-X

Solvent

7.36

5.84

-C≡N

CCl 4

Cinnamonitrile

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Nitriles Aromatics

A large amount of chemical shift data is available for this commercially important group of compounds. The nitrile group is a weak deshielder of aliphatic and aromatic protons, similar to several other unsaturated carbon-carbon and carbon-nitrogen functional groups. Fortunately, the nitrile group is easily characterized by its infrared absorption band allowing the NMR analyst to concen-trate his energies on the proton groups in the molecules which are less easily defined by the infrared data.

Aromatic Protons Benzonitrile

(ppm)

X

Solvent

7.20-7.75

-C≡N

CCl4

para-Substituted Benzonitriles

δ

b

(ppm)

δ

a

(ppm)

para

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Solvent

The Sadtler Handbook of Proton NMR Spectra

7.35

6.58

CDCl3

7.66

7.17

-F

CDCl3

7.47

7.23

-CH3

CCl4

7.57

7.39

-Cl

CDCl3

7.90

7.90

TFA

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Cyanamides

Although the Cyanamid group is of commercial importance, relatively few hydrocarbon derivatives are available for study. The chemical shifts of the aliphatic groups bonded to the Cyanamid group display intermediate deshielding similar to that of the corresponding amines.

Aliphatic Protons

δ

b

(ppm)

δ

a

(ppm)

X

(2.88)

Solvent CCl4

(1.29)

CDCl3

Diallylcyanamide

δ

bc

(ppm)

(5.0-6.2)

δ

a

(ppm)

Compound

3.60

Dibenzylcyanamide

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Solvent

CCl4

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δ

a

(ppm)

4.06

Compound

Solvent

CDCl3

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Isocyanides

This rather rare functional group is one of the few that may display coupling (2n + 1) between the Nitrogen nucleus and adjacent hydrocarbon groups.

Aliphatic Protons Benzyl isocyanide

δ

b

(ppm)

δ

ca 7.33

a

(ppm)

Compound

4.59

Solvent

CDCl3

Alicyclic Protons Cyclohexyl isocyanide

δ

b

(ppm)

δ

a

(ppm)

Compound

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Solvent

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0.90-2.27

3.60

CDCl3

Coupling and Coupling Constants J C≡N-CH2 = 2.1 Hz

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Thiocyanates

The thiocyanate group has an intermediate deshielding effect on adjacent aliphatic groups but little or no shielding/deshielding effect on the aromatic protons. It is similar to many of the preceding groups in that it is difficult to determine the presence of this group in an NMR spectrum with any degree of certainty, without additional information such as elemental analysis data or infrared information.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

1.51 0.99

(1.2-2.1)

δ

a

X

(ppm)

2.61

CCI4

3.00

CDCI3

2.97

CH3-(CH2)2-CH2-S-C≡N

Substituted Methyl Thiocyanates

δ

a

(ppm)

-X

Solvent

Solvent

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CCI4

The Sadtler Handbook of Proton NMR Spectra

3.58

CDCI3

4.15

CDCI3

4.23

CDCI3

4.40

CDCI3

-S-C≡N

CDCI3

4.67

4.92

-Cl

CCI4

Substituted Ethylthiocyanates

δ

b

(ppm)

δ

a

X

(ppm)

3.01

2.01

3.38

3.38

3.11

3.78

Solvent CDCI3 Polysol

-S-C≡N

CCI4

Aromatic Protons Substituted Phenylisocyanates

δ

e

(ppm)

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Solvent

6.92

6.71

NH2

O-R2

7.00

Polysol

7.22

6.89

OH

CH3

7.30

DMSO-d6

7.12

CH3

OH

CH3

7.12

CDCI3

7.30

CH3

OH

6.89

7.22

DMSO-d6

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7.35

6.68

OH

CH3

CH3

7.48

7.03

NH2

7.41

DMSO-d6

7.92

7.61

Cl

8.01

CDCI3

7.93

8.12

8.36

8.25

8.69

8.99

S-C≡N

CDCI3

CDCI3

DMS

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Nitroso Compounds

The data for the aliphatic Nitroso compounds is confusing. The spectrum of 2-methyl-2-nitrosopropane presents a puzzle in that two bands are observed with an intergration ratio of approximately 2:1. One explanation may be that there is restricted rotation about the C-N bond producing a different chemical shift for one of the tert-butyl methyl groups. Such restricted rotation may also be observed in the spectra of the aromatic compounds in that the protons ortho to the N=O group are always slightly broadened in comparison to the other protons in the aromatic ring. The effect of the Nitroso group on the chemical shifts of the ortho aromatic compounds is that of a strongly deshielding group.

Aromatic Protons Para substituted nitroso benzenes

δ b (ppm)

δ

a

(ppm)

-X -O-Na

Solvent

7.73

6.52

D2O

7.70

6.60

7.67

6.63

7.77

7.08

Polysol

7.79

6.65

CDCI3

CDCI3

-OH

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Acetone

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N-Nitroso Compounds

Non-equivalence of similar groups bonded to the nitrosoamine nitrogen nucleus is a character-istic of these compounds. Due to restricted rotation about the N —N bond the groups bonded to the amine nitrogen can reside either syn or anti to the nitroso oxygen atom producing a differ-entiation in their chemical shifts. The group syn to the oxygen atom usually resonates at higher field and may display a certain degree of broadening in comparison to the group in the anti position. The differentiation in chemical shift decreases with distance from the amine nitrogen atom, i.e. the alpha groups differ in chemical shift by about 0.6 ppm, the beta groups by about 0.3 ppm and the gamma groups by about 0.1 ppm.

Aliphatic Protons

δ

c

(ppm)

δ b (ppm)

δ

a

(ppm)

X

Solvent

(2.95)

CCI4

(syn) (3.71)

CCI4

(anti) CDCI3

3.60) (1.11 (syn) 4.12)

CDCI3

(1.41 (anti)

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The Sadtler Handbook of Proton NMR Spectra

CCI4

3.48) (0.88

1.50 (syn) 4.06)

(0.97

CCI4

1.80 (anti)

Aromatic Protons The N-nitroso group deshields all of the aromatic hydrogens of the anti ring forming a complex, higher order pattern centered at about 7.45 ppm. In some examples, two ortho hydrogens are slightly shielded and probably represent the ortho hydrogens of the ring syn to the N-nitroso oxygen atom.

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Nitrates

The Nitrates which contain the –O-NO2 substituent produce lower field shifts than the corresponding N-Nitro compounds. The effect of the – O -NO2 group is not as strongly deshielding, however, as the –O-N=O group of the Nitrites. Several comparisons of the Nitrate and Nitrite chemical shifts are presented below.

Aliphatic Protons

(ppm)

δ c

(ppm)

δ b

1.01

1.75

0.97

1.72

(ppm)

δ

Compound

Solvent

a 4.40

CCI 4

4.61

CCI 4

5.15

CCI

5.59

CCI 4

4.47

CDCI

4

(1.37)

(1.40)

3

1.74

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Nitrites

The nitrite group is one of the most strongly deshielding substituents in its effect on the alpha aliphatic groups. Methylene groups are deshielded to about 4.5 ppm and methines to about 5.5 ppm. Such extremes of chemical shift are characteristic of only a few substituents making the identification of a Nitrite compound a relatively easy matter.

Aliphatic Protons

δ

c

(ppm)

0.97

δ

b

(ppm)

δ

a

(ppm)

Compound

1.72

4.61

CCI4

(1.40)

5.59

CCI4

CDCI3

(1.57)

(0.98)

Solvent

1.98

4.45

CCI4

Coupling and Coupling Constants The nitrite compounds display no unusual coupling nor coupling constants. The normal vicinal aliphatic proton coupling of about 7 Hz is observed.

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The Sadtler Handbook of Proton NMR Spectra

Solubility and Solvent Effects The aliphatic nitrites are readily soluble in the halogenated NMR solvents; carbon tetrachloride and deuterochloroform. No special solvent effects have been noted.

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Nitro Compounds Aliphatics

The nitro functional group is one of the very few substituents which strongly deshield both adjacent aliphatic groups and the ortho aromatic protons. The group imparts no other distinguishing characteristics to the proton NMR spectrum.

Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent

4.22

CCI4

4.40

CCI4

4.31

CCI4

4.65

CDCI3

1.55

1.01

2.00

(1.57)

CCI4 (1.61)

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Nitro Compounds Aromatics

The nitro functional group is one of the very few substituents which strongly deshield both adjacent aliphatic groups and the ortho aromatic protons. The group imparts no other distinguishing characteristics to the proton NMR spectrum.

Aromatic Protons Nitrobenzene

δ

b

(ppm)

δ

a

X

(ppm)

Solvent CCI4

8.20

7.3-7.8

Para-Substituted Nitrobenzenes

δ

b

(ppm)

δ 7.84

a

(ppm)

6.19

para -O-Na

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Solvent DMSO

The Sadtler Handbook of Proton NMR Spectra

8.09

6.67

-NH2

DMSO-d6

8.12

6.91

-O-CH3

CCI4

8.15

7.06

-OH

8.05

7.09

8.20

7.20

-F

CCI4

8.10

7.30

-CH3

CDCI3

8.19

7.32

-N=C=S

CDCI3

8.09

7.46

-Cl

CDCI3

8.03

7.62

-Br

CDCI3

7.78

7.62

DMSO

8.26

7.82

Acetone

Acetone Acetone

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N-Nitro Compounds

The addition of a nitro group as one of the groups bonded to an amine nitrogen atom increases the deshielding effect of the amine group. The presence of the N-Nitro group also decreases the relative solubility of these compounds in comparison to the corresponding amines.

Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent CDCI3

0.90

2.25

3.61

CDCI3 3.71

4.01

Polysol 3.65

Alicyclic Protons

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The Sadtler Handbook of Proton NMR Spectra

δ

a

(ppm)

4.01

Compound

Solvent

DMSO-d6

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Silicon Compounds

The outstanding characteristic of the silicon compounds is the extremely high-field chemical shifts observed for aliphatic groups bonded to the silicon nucleus. These aliphatic groups resonate at higher fields than any other group in corresponding molecular structures. Additionally, coupling between Si—H protons and adjacent aliphatic groups is observed as clear n+1 multiplets. The silicon compounds are readily soluble in all the normal NMR solvents excluding D2O. The chemical shifts of groups bonded to the oxygen atom of the silicon ethers (siloxanes) are described with the other ether oxygen compounds.

Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

X

Solvent

(0.00)

(0.03)

CCI4

(0.04)

CCI4

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(0.06)

C2CI4

(0.12)

CCI4

(0.29)

CDCI3

(0.40)

C2CI4

(0.48)

CDCI3

(0.63)

CCI4

0.77

CDCI3

(0.80)

CDCI3

1.17

CCI4

0.56)

CCI4

(0.92

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The Sadtler Handbook of Proton NMR Spectra

1.30

CDCI3

0.90

CDCI3

1.10

0.90

(1.1-1.7)

Substituted Methyl Silanes

X (ppm)

δ

a

(ppm)

-Si(X,Y,Z)

Solvent CDCI3

R2-

0.67

CCI4 R5-

0.90

C2CI4 CH2-CH=CH2-

1.52

CCI4 CH2=CH-

1.56

CDCI3

2.59

CCI4 Cl-

2.69

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The Sadtler Handbook of Proton NMR Spectra

CDCI3

2.91

CDCI3 Cl-

3.11

Silane Protons Si-H (ppm)

Compound

Solvent

3.52

CDCI3

4.03

CDCI3

4.14

CCI4

4.46

CCI4

4.92

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

5.39

CDCI3

5.54

CCI4

5.79

CCI4

Olefinic Protons The silicon nucleus deshields all three of the vinyl protons producing a complex ABC pattern centered at about 5.9 ppm.

Aromatic Protons Silicon substituents deshield the ortho aromatic hydrogens which resonate in the range 7.5-7.8 ppm depending on the other groups attached to the silicon nucleus. The chemical shifts of a few re-presentative aromatic silanes are provided.

Phenyl Silanes

δ

abc

(ppm)

7.10-7.60

-Si(X,Y,Z)

Solvent CCI4

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The Sadtler Handbook of Proton NMR Spectra

δ

7.10-7.60

CDCI3

7.20-7.65

CDCI3

7.10-7.70

CDCI3

bc

(ppm)

δ

a

(ppm)

-Si(X,Y,Z)

Solvent

7.1-7.5

7.48

CCI4

7.1-7.4

7.48

CDCI3

7.1-7.4

7.54

CDCI3

7.1-7.4

7.56

CDCI3

7.1-7.5

7.60

CCI4

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The Sadtler Handbook of Proton NMR Spectra

7.0-7.4

7.62

CDCI3

7.2-7.7

7.81

CDCI3

Para Substituted Phenylsilanes

X-

δ

b

(ppm)

δ

a

(ppm)

para

Solvent

CH3-O-

6.85

7.40

CDCI3

CH3-O-

6.83

7.41

CDCI3

Cl-

7.35

7.51

CCI4

7.33

7.62

CDCI3

Coupling and Coupling Constants Coupling between the silane protons and adjacent aliphatic groups is observed as clear n+1 multiplets.

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The Sadtler Handbook of Proton NMR Spectra

J H-Si-CH2

=

3.1-3.9 Hz

The isotope silicon-29 has a natural abundance of 4.7% and possesses a spin of 1/2. These isotope sidebands can often be observed in the spectra of the silanes if the noise level of the baseline is suf-ficiently low to allow their definition. J29Si-H3 = 184 Hz J29Si-H2 = 199 Hz

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Phosphorus Containing Compounds Phosphines

For the sake of comparison, this group of compounds includes not only the Phosphines, but also several other trivalent phosphorus compounds. The phosphine phosphorus nucleus is a very weakly deshielding substituent in its effect on adjacent aliphatic groups, similar in effect to another ali-phatic group (CH3, CH2, CH). Its effect on the aromatic protons varies, depending on the other groups bonded to the phosphorus nucleus, from a weakly deshielding to a strongly deshielding group. Coupling between the phosphorus atom and adjacent protons is usually present but often difficult to see clearly due to overlap with noncoupled protons.

Aliphatic Protons

δ

d

(ppm)

0.94

δ

c

(ppm)

δ

b

(ppm)

(1.1-1.9)

1.05

δ

a

(ppm)

Compound

Solvent

1.1-1.9

CDCl3

1.99

CDCl3

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The Sadtler Handbook of Proton NMR Spectra

CDCl3

1.53

Aromatic Protons Phenyl Phosphines

δ

δ

ab

-X

(ppm)

Solvent

6.99-7.44

CDCI3

7.12-7.59

CCI4

7.00-7.60

CCI4

7.10-7.60

CDCI3

b

(ppm)

δ

a

(ppm)

-X

Solvent

7.1-7.5

CDCl3 7.60

7.1-7.6

7.83

CDCI3

CCI4

7.3-7.7 8.19

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The Sadtler Handbook of Proton NMR Spectra

The phosphorus nucleus of the phosphine compounds couples weakly, if at all, with an alpha ali-phatic group, strongly with the beta aliphatic group, and weakly with the gamma group. Certain anomalies appear to exist in the data for those compounds in which two phosphine groups are present. Due to the small number of compounds available for analysis, the data is presented as it was deduced from the spectra via first order analysis.

J31P-CH

J31P-C-CH

= 0 Hz

J31P-CH

J31P-C-CH

J

2

2

= 0 Hz

= 9.5 Hz

P-CH

= 4-5 Hz,

P-CH

= ca 1 Hz

Aromatic Protons

Jortho = 8.5 Hz

J P-C-C-CH3

=

= 17 Hz

= 4.0 Hz

J31P-CH

J

3

1-2 Hz

Phosphine Oxides

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JP-C-CH

2

= 4.5 Hz

The Sadtler Handbook of Proton NMR Spectra

The Phosphine Oxide group produces chemical shifts similar to those of the phosphines but with a significant increase in the magnitude of the coupling constants to the alpha hydrocarbon group. The long chain aliphatic phosphine oxides are often difficult to distinguish from the simple alkanes due to the weak carbon-like deshielding of the alpha methylene group.

Aliphatic Protons

δ

m

(ppm)

δ -δ (ppm) l b

δ

-X

Solvent

(1.44)

(CH3)2-P(=O)-R13

CDCl3

a

(ppm)

0.89

(1.1-1.5)

~1.5

CH3-(CH2)11-CH2-P(=O)(CH3)

CDCl3

-X

CH - (ppm) 2

-P (=O)

-X,Y

Solvent

R-

2.59

-P(=O)

CDCl3

3.00

-P(=O)

CDCl3

Aromatic Protons

The Phosphine Oxide group is a moderately strong deshielding group in its effect on the ortho aromatic hydrogens. Coupling to these hydrogens, when it can be observed, is found to be about 12-13 Hz. δ

b

(ppm)

δ

a

(ppm)

-X

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Solvent

The Sadtler Handbook of Proton NMR Spectra

7.3-7.7

7.72

CDCl3

Coupling and Coupling Constants

JP-CH

3

JP-CH

2

=

12-13 Hz

=

10-12 Hz

Phosphonium Compounds

The phosphorus nucleus of the phosphonium compounds is a much more strongly deshielding group than that of the phosphines. Clear coupling to the alpha aliphatic groups is observed which makes this group of compounds more easily identifiable than the phosphines. Although soluble in deutero-chloroform, the spectra as a group suffer from a slightly higher noise level than the other phosphorus containing compounds due to their lower solubility.

Aliphatic Protons

δ

d

(ppm)

0.94

δ

c

(ppm)

(1.1-2.0)

δ

(ppm) b (1.33

δ

(ppm) a 2.52)

Compound

2.55

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Solvent ¯I

CDCl3

¯ Cl

CDCl3

The Sadtler Handbook of Proton NMR Spectra

(1.16

0.89

1.71

(1.3-1.9)

1.24

1.79

(2.74)

¯ Br

CDCl3

3.08)

¯ Br

CDCl3

3.27

¯ Br

CDCl3

3.69

¯ Br

CDCl3

3.70

¯ Br

CDCl3

Substituted Methanes (X,Y,Z)

-P+-

δ

a

(ppm)

-X

Solvent

-P+-

4.13

¯ Br

CDCl3

-P+-

4.43

¯ Cl

CDCl3

-P+-

4.58

¯ Br

CDCl3

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The Sadtler Handbook of Proton NMR Spectra

-P+-

4.77

¯ Br

CDCl3

Aromatic Protons The phosphonium group deshields all of the aromatic hydrogens producing a complex, higher order band at low field.

p,m,o (ppm)

-X

Solvent

7.62-8.08

¯ Br

CDCl3

¯I

CDCl3

¯ Br

CDCl3

7.50-8.10 7.50-8.20

Coupling and Coupling Constants J + P - CH3 = 13.6 Hz J + P -CH2 = 13.0-15.1 Hz J + P -C-CH3 = 18.2 Hz

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Sulfides Aliphatics

The sulfide linkage has a weakly deshieding effect on adjacent aliphatic groups and a weak shielding effect on the ortho aromatic hydrogens. In both cases, the phenyl sulfide group is a more strongly deshielding group than the corresponding aliphatic sulfide linkage. Except in the case of the heterocyclic molecules, the coupling constants are the same as those ob-served for the other substituents discussed thus far.

Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Compound

1.90

Solvent CCI4

2.01

CH3-S-R12

CCI4

2.04

CH3-S-R2

CCI4

2.06

CH3-S-CH3

CCI4

2.29

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CCI4

The Sadtler Handbook of Proton NMR Spectra

2.39

CDCI3

2.45

CDCI3

1.19

2.32

CCI4

1.23

2.43

CH3-CH2-S-CH3

CCI4

2.47

CH3-CH2-S-R3

CCI4

1.23

0.98

(0.99)

1.23

2.68

1.59

2.44

(1.38)

3.12

TFA

1.79

2.32

CCI4

CCI4

CH3-CH2 -CH2-S-R

CCI4

(1.36)

CCI4

Substituted Methylsulfides

δ

a

-X

(ppm)

Solvent CCI4

2.32

2.43

-CH3

CCI4

3.09

-CH=CH2

CDCI3

3.36

-C≡N

CCI4

3.77

CDCI3

3.80

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

3.80

4.83

δ

a

CCI4

-Cl

CDCI3

-X

(ppm)

Solvent

2.10

CCI4

3.49

CCI4

3.58

CDCI3

-C≡C-R

3.59

CDCI3

3.99

CDCI3

4.00

PolysoI

4.10

CDCI3

4.67

PolysoI

Substituted Ethylsulfides

δ

b

(ppm)

δ

a

-X

(ppm)

2.44

1.59

2.52

1.69

-CH3

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Solvent CCI4 CDCI3

The Sadtler Handbook of Proton NMR Spectra

δ

2.55

2.66

2.71

2.71

-S-R2

CCI4

2.75

2.88

-C≡N

CDCI3

2.61

3.63

-OH

b

(ppm)

δ

a

CCI4

CCI4

-X

(ppm)

Solvent

2.70

2.70

Polysol

3.10

2.58

Polysol

3.11

2.78

Polysol

3.07

2.90

CDCI3

2.89

3.57

-OH

CCI4

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Sulfides Aromatics

The sulfide linkage has a weakly deshieding effect on adjacent aliphatic groups and a weak shielding effect on the ortho aromatic hydrogens. In both cases, the phenyl sulfide group is a more strongly deshielding group than the corresponding aliphatic sulfide linkage. Except in the case of the heterocyclic molecules, the coupling constants are the same as those ob-served for the other substituents discussed thus far.

Aromatic Protons Phenyl Sulfides

(ppm) 6.90-7.30

-X -S-CH3

Solvent CDCI3

7.00-7.43

CCI4

7.10-7.70

CDCI3

Para Substituted Phenylsulfides

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The Sadtler Handbook of Proton NMR Spectra

δ

δ

b

b

(ppm)

(ppm)

-X

7.22

6.75

-OH

7.10

6.83

-NH-R

7.05

7.05

-CH3

7.11

7.39

-Br

7.21

7.55

7.24

7.81

Polysol

7.27

7.89

DMSO-d6

(ppm)

δ

δ

a

a

Solvent CDCI3 Polyso I CCI4 CDCI3 DMSO-d6

(ppm)

-X

Solvent

7.33

6.63

CDCI3

7.23

6.78

-NH2

Polysol

7.08

6.94

-O-CH3

CDCI3

7.28

7.28

-Cl

7.21

7.07

-CH3

CDCI3

7.47

7.47

-NH2 (salt)

TFA

7.44

7.97

Polysol

CDCI3

Thiophenes Due to the small differentiation in chemical shift between the protons of the parent compound and the relatively large coupling constants involved, the multiplets that arise from the substituted thiophenes are usually higher order in character. The coupling constants are unusual in that the J2-3 coupling constant is normally larger than the J3-4 situation that does not occur in the spin-spin interactions of the corresponding oxygen and nitrogen heterocyclics.

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The Sadtler Handbook of Proton NMR Spectra

δ

b

(ppm)

δ

6.90

a

(ppm)

Solvent

7.10

CCl4

2-Substituted Thiophenes

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Solvent

7.03

6.87

6.72

-CH3

CDCI3

6.92

6.72

6.72

-Cl

CDCI3

7.12

6.79

6.98

-Br

CCI4

7.19

6.72

7.27

-I

7.53

7.02

7.53

7.60

7.10

7.60

7.54

7.07

7.62

CCI4

7.62

7.07

7.71

CDCI3

7.67

7.12

7.67

CCI4

7.56

7.07

7.69

D2O

CDCI3

CCI4

-C≡N

3-Substituted Thiophenes

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CDCI3

The Sadtler Handbook of Proton NMR Spectra

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Solvent

6.75

-C3

6.78

7.05

6.77

-CH3

6.77

CCI4

7.18

6.91

-Br

7.11

CDCI3

7.11

CCI4

Coupling and Coupling Constants J 2-3 = 3-4 Hz J 3-4 = 4-5 Hz J 2-4 = 1-2 Hz

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Disulfides

The disulfide group produces chemical shifts similar to those of the sulfides. Its effect on the adjacent aliphatic groups is slightly more deshielding by about 0.10.4 ppm while its effect on the ortho aromatic protons is slightly less deshielding by about 0.2 ppm. Without prior knowledge that the element sulfur was present in the molecular formula of an unknown material, both linkages would be difficult to identify because of their weakly deshielding character, their lack of exchangeable protons and the fact that no unusual coupling constants are observed, with the exception of thiophene.

Aliphatic Protons

δ

c

(ppm)

δ b (ppm)

δ

a

(ppm)

2.39

Compound CH3-S-S-CH3

2.33

Solvent CCI4 CCI4

2.66

CDCI3

CDCI3

1.25

0.93

1.70

2.69

0.99

(1.2-2.2)

2.96

CDCI3

2.55

CCI4

2.98

CDCI3

(1.01)

1.92

(1.30) CCI4 (1.30)

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The Sadtler Handbook of Proton NMR Spectra

Substituted Methyldisulfides

δ

a

-X

(ppm) 2.70

-CH3

3.29

-CH=CH2

Solvent CDCI3 CCI4 CS2

3.46

CCI4 3.51

TFA

3.70

Polysol

3.70

Substituted Ethyldisulfides

δ

b

(ppm)

δ

a

X

(ppm)

2.69

1.70

2.89

2.65

3.07

3.39

2.86

3.49

-CH3

Solvent CDCI3 DMSO-d6

-NH2(HCI)

D2O Polysol

Aromatic Protons Phenyl Disulfides

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The Sadtler Handbook of Proton NMR Spectra

δ CH3-S-S-

b

(ppm)

δ

a

Solvent

(ppm)

7.10-7.35

7.45

CCI4

7.00-7.35

7.46

CDCI3

Para Substituted Diphenyl Disulfides

δ

b

(ppm)

δ

a

X

(ppm)

Solvent

7.12

6.55

-NH2

DMSO-d6

7.48

6.86

-O-CH3

CDCI3

7.34

7.05

-CH3

CDCI3

7.38

7.20

-Cl

CDCI3

7.39

7.39

-Br

7.48

7.65

DMSO-d6

7.51

7.99

CDCI3

7.79

8.07

DMSO-d6

CDCI3

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Thiols Aliphatics

The aliphatic thiols are an especially easy group of compounds to characterize due to the clear coupling between the thiol proton (-S-H) and adjacent aliphatic groups (except in D2O solution). The aromatic thiols are also relatively easy to characterize in that they contain an exchangeable proton which resonates at relatively high field (3.0-5.0 ppm) but the group does not strongly shield the ortho and para hydrogens as the aromatic amines and phenols do. The thiol group is a weak to intermediate deshielding group in its effect on aliphatic protons but neither shields nor deshields the ortho aromatic hydrogens to any great extent.

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

X

Solvent

2.07

1.24

CH3-SH

CDCl3

1.31

2.52

1.17

CH3-CH2-SH

CCl4

1.67

2.52

1.31

CH3-CH2-CH2-SH

CCl4

(1.31)

3.07

0.99

1.40

TFA

1.62

CCl4

(1.41)

Substituted Methanethiols

δ

b

(ppm)

1.99

δ

a

(ppm)

3.20

X

Solvent CCI4

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The Sadtler Handbook of Proton NMR Spectra

2.22

3.31

2.06

CDCI3

CDCI3

3.33

2.06

3.41

CDCI3

3.51

D2O

1.58

3.57

CCI4

1.50

3.64

CCI4

Substituted Ethanethiols

δ

c

(ppm)

δ

b

(ppm)

δ

a

-X

(ppm)

Solvent

1.12

2.43

0.67

CCI4

1.18

2.50

1.60

CCI4

1.19

2.49

1.60

-R4

CCI4

1.31

2.52

1.67

-CH3

CDCI3

1.18

2.51

1.69

CCI4

1.30

2.51

1.84

CDCI3

-CH2-SH

CCI4

1.27

2.67

1.89

1.58

2.54

2.30

2.71

2.71

-SH

D2O

2.68

3.69

-OH

D2O

CDCI3

Aromatic Protons

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The Sadtler Handbook of Proton NMR Spectra

δ

b

(ppm)

δ

3.19

~6.91

a

(ppm)

(broad, single, peak)

Para Substituted Benzenethiols

δ

c

(ppm)

3.52

δ

b

(ppm) 7.14

δ

a

-X

(ppm)

Solvent

6.52

-NH2

CDCI3

3.37

7.30

6.81

-O-CH3

CDCI3

3.30

7.09

6.91

-CH3

CDCI3

3.40

7.11

7.11

-Cl

CDCI3

3.16

7.13

7.13

3.42

7.07

7.30

CCI4

-Br

CDCI3

Exchangeable Protons The thiol protons, being less active than the exchangeable hydrogens of the amines and alcohols, usually display coupling to the adjacent aliphatic groups in all solvents except D2O. One exception to this fact occurs in the case in which another type of exchangeable is present in the molecule. The thiol-aliphatic group coupling constant is similar to that observed for vicinal CH—CH coupling, J = 5-8 Hz. These protons undergo deuteration only slowly upon the addition of a few drops of D2O to a sample solution of CDCI3 or CCI4 . In D2O solution, however, they exchange completely and immediately.

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Thiols Aromatics

The aromatic thiols are also relatively easy to characterize in that they contain an exchangeable proton which resonates at relatively high field (3.0-5.0 ppm) but the group does not strongly shield the ortho and para hydrogens as the aromatic amines and phenols do. The thiol group is a weak to intermediate deshielding group in its effect on aliphatic protons but neither shields nor deshields the ortho aromatic hydrogens to any great extent.

Aromatic Protons

δ

b

(ppm)

δ

3.19

a

(ppm)

~6.91 (broad, single, peak)

Para Substituted Benzenethiols

δ

c

(ppm)

δ

b

(ppm)

δ

a

-X

(ppm)

Solvent

3.52

7.14

6.52

-NH2

CDCI3

3.37

7.30

6.81

-O-CH3

CDCI3

3.30

7.09

6.91

-CH3

CDCI3

3.40

7.11

7.11

-Cl

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

3.16

7.13

7.13

3.42

7.07

7.30

CCI4

-Br

CDCI3

Exchangeable Protons The thiol protons, being less active than the exchangeable hydrogens of the amines and alcohols, usually display coupling to the adjacent aliphatic groups in all solvents except D2O. One exception to this fact occurs in the case in which another type of exchangeable is present in the molecule. The thiol-aliphatic group coupling constant is similar to that observed for vicinal CH—CH coupling, J = 5-8 Hz. These protons undergo deuteration only slowly upon the addition of a few drops of D2O to a sample solution of CDCI3 or CCI4 . In D2O solution, however, they exchange completely and immediately.

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Sulfoxides

The Sulfoxide group imparts no special features to its NMR spectrum. It is an intermediate to strong deshielder of adjacent aliphatic groups and a weak to intermediate deshielder of the ortho aromatic hydrogens. Dimethyl Sulfoxide is well known as a solvent, with its deuterated form a commonly used material in NMR. All of the unsubstituted sulfoxides are readily soluble in the chlorinated solvents such as CCI4 and CDCI3.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

2.52

Compound

Solvent CCI4

CCI4 1.28

2.56

CCI4 1.02

1.66

2.67

(1.1-2.0)

(1.1-2.0)

2.51

(1.1-2.1)

(1.1-2.1)

2.68

0.99

0.96

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CCI4

CDCI3

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CCI4 (1.22)

2.67

Aromatic Protons Phenyl Sulfoxides

X-

δ

a

Solvent

(ppm)

7.30-7.70

CCI4

7.25-7.80

CDCI3

Para-Substituted Phenylsulfoxides

δ

b

(ppm)

δ

a

(ppm)

-X

Solvent CDCI3

7.56

6.93

-O-CH3

7.86

7.36

-I

7.61

7.54

-Cl

CDCI3

CDCI3

CDCI3 7.86

8.42

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Sulfones

In comparison to the sulfoxides (-S(=O)-), the sulfones (-S(=O)2-) are a more strongly deshielding substituent in their effect on both the adjacent aliphatic groups and on the ortho aromatic protons. Some of the relative deshielding effect of the sulfur containing functional groups are displayed. 1.90 2.39 2.52 2.87

ppm ppm ppm ppm

CH3-S-R CH3-S-S-R CH3-S(=O)-R CH3-S(=O)2-R

The compounds containing the sulfone group are somewhat less soluble in the chlorinated solvents than the sulfoxides but, are more soluble in solvents such as acetone, DMSO-d6, Polysol and D2O.

Aliphatic Protons

δ

d

(ppm)

0.97

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent

2.87

CDCl3

3.11

D2O

1.26

2.97

CCl4

1.09

1.81

2.91

CCl4

(1.2-2.1)

(1.2-2.1)

2.95

CDCl3

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Substituted Methanesulfones

δ

a

X

(ppm)

Solvent

3.80

-CH=CH2

CDCI3

4.30

-C≡C-R

Polysol

4.35

-C≡C-H

Polysol

4.44

Polysol

4.60

Polysol

4.88

Polysol

Olefinic Protons The sulfone group deshields all three vinyl protons, producing a complex, higher order pattern in the chemical shift range from 6.0-7.0 ppm. Analysis of these patterns suggests that the proton trans to the SO2 group resonates at highest field (about 6.2 ppm), that the proton cis to the SO2 group resonates at slightly lower field (about 6.4 ppm), and that the geminal proton resonates at lowest field (about 6.8 ppm).

Aromatic Protons The sulfone substituted phenyl groups produce an aromatic pattern characteristic of a substituent which strongly deshields the ortho protons. The para and meta hydrogens overlap to produce a complex multiplet in the range from about 7.2-7.8 ppm while the ortho hydrogens appear as a higher order doublet of doublets at about 7.9 ppm.

Phenylsulfones

δ

b

(ppm)

7.2-7.7

δ

a

(ppm)

-X

7.89

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Solvent CDCl3

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7.2-7.8

8.02

CDCl3

Para-Substituted Phenylsulfones

δ

δ

b

b

(ppm)

δ

a

-X

(ppm)

Solvent

7.85

7.11

-O-CH3

Polysol

7.78

7.34

-CH3

CDCI3

7.81

7.50

-Cl

CDCI3

(ppm)

δ

a

-X

(ppm)

Solvent

7.79

6.91

-O-CH3

CDCI3

7.95

7.18

-F

CDCI3

7.80

7.23

-CH3

CDCI3

7.82

7.42

-Cl

CDCI3

7.82

7.65

-Br

CDCI3

8.08

8.30

CDCI3

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Sulfonyl Halides

We present chemical shift data only for the sulfonyl fluorides and chlorides. While the type of halogen present appears to have a significant effect on the chemical shifts of aliphatic groups, the effect is much less pronounced in relation to the ortho aromatic hydrogens. For the sake of comparison, a series of methyl substituted SO2 groups of various types is presented.

δ

a

(ppm)

2.82

Compound

Solvent D2O

3.03

Polysol

3.07

CDCI3

3.11

D2O

3.49

DMSO-d6

3.65

CCI4

It is interesting to note that when the sulfonyl chloride undergoes hydrolysis to form the corresponding sulfonic acid, the methyl resonance is converted from the most strongly deshielded (3.65 ppm) to the least deshielded group of this series (2.82 ppm).

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Aliphatic Protons

δ

d

(ppm)

δ

1.02

c

(ppm)

δ

b

(ppm)

δ

a

X

(ppm)

Solvent

3.65

CH3-SO2-CI

CCl4

1.54

3.65

CH3-CH2-SO2-CI

CS2

1.17

2.09

3.68

CH3-CH2-CH2-SO2-CI

CCl4

1.50

2.00

3.69

CH3- CH2-CH2-CH2-SO2-CI

CCl4

Substituted Methane Sulfonyl Halides

-X

δ

a

-Y

(ppm)

Solvent

4.83 CDCI3

5.07 Polysol

Aromatic Protons Both the chlorine and fluorine sulfonyl compounds strongly deshield the ortho aromatic hydrogens. The chemical shifts observed for the two phenyl compounds are extremely similar. A comparison of the para substituted compounds indicates identical shifts for the two para substituted methyl compounds, higher field shifts for the chlorine substituted sulfonyl fluoride but lower field shifts for the corresponding carboxylic acid substituted sulfonyl fluoride compared to the corresponding sulfonyl chlorides.

Phenylsulfonyl Halides

δ

a

(ppm)

Solvent

8.03 CCl4

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8.00 CCl4

Para-Substituted Phenylsulfonyl Halides

δ

δ

b

b

(ppm)

δ

a

(ppm)

-X

Solvent

7.98

7.07

-O-CH3

CDCI3

7.90

7.41

-CH3

CDCI3

8.05

7.67

-Cl

CDCI3

7.99

7.69

-I

CDCI3

7.90

7.77

-Br

CDCI3

8.17

8.08

CDCI3

7.90

8.09

Polysol

8.13

8.13

Polysol

8.01

8.28

Polysol

(ppm)

δ

a

(ppm)

-X

Solvent

7.73

6.71

-NH2

CDCI3

7.90

7.41

-CH3

CDCI3

7.98

7.62

-Cl

CDCI3

8.01

8.01

DMSO-d6

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8.13

8.13

Polysol

8.14

8.33

Polysol

Coupling and Coupling Constants The only unusual coupling constant associated with the sulfonyl halides is that observed between the sulfonyl fluoride group and the adjacent-aliphatic group J

F-S(O2)-CH2 = 4.5 Hz

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Sulfonic Acids

The sulfonic acids are similar to the other sulfone (-S(O2)-) compounds in their chemical shift effects, in that, they are a moderately strong deshielding group for adjacent aliphatic groups and a strong deshielding group for ortho aromatic hydrogens. The lower molecular weight members of the series are soluble in both the chlorinated solvents as well as DMSO-d6, polysol and D2O. When an amine group is present in the molecule, they form an internal salt which makes these compounds soluble almost exclusively in D2O or DMSO-d6.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

a

X

(ppm)

D2O

2.82

1.45

0.97

CDCI3

3.24

1.90

1.55

CCI4

3.26

1.97

1.11

CDCI3

3.23

Substituted Ethanesulfonic Acids

δ

b

(ppm)

δ

a

(ppm)

-X

Solvent

Solvent

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3.42

3.30

-NH-CH3

D2O

3.51 D2O

3.51

3.40

3.27

-NH2

D2O

Sulfonic Acid Protons

δ

a

-X

(ppm)

Solvent

8.75

CCI4

10.70

-R2

CCI4

10.71

-R

3

CDCI3

10.72

-R4

CDCI3

Aromatic Protons The sulfonic acid group strongly deshields the ortho aromatic hydrogens. The ortho protons resonate near 7.9 ppm as a distorted doublet of doublets while the meta and para hydrogens appear as a complex higher order band in the chemical shift range from 7.4-7.7 ppm.

Benzenesulfonic acid

δ

b

(ppm)

7.93

δ

a

(ppm)

7.4-7.7

Solvent D2 O

Para-Substituted benzenesulfonic acids

δ

b

(ppm)

δ

a

(ppm)

-X

Solvent

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DMSO-d6

7.61 7.19 7.81

7.81

-CH3 DMSO-d6

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Salts of Sulfonic Acid

The water soluble metallic salts of sulfonic acid display aromatic chemical shifts very similar to those of the free acid with the aliphatic groups adjacent to the suIfonate group resonating at slightly higher field. Although of commercial importance, relatively small number of compounds are available for the preparation of their NMR spectra.

Aliphatic Protons

δ

d

(ppm)

0.91

δ

c

(ppm)

δ

b

(ppm)

(1.2-1.6)

δ

1.72

a

Compound

(ppm) 2.87

D2O

2-Substituted Ethanesulfonic Acid Salts

δ

b

(ppm)

δ

a

(ppm)

Solvent

X

Solvent D2O

2.89

1.72

-R3

3.15

2,96

-C≡N

D2O

3.27

3.27

-SO3-Na

D2O

3.41

3.66

-Br

D2O

3.37

3.89

-Cl

D2O

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The Sadtler Handbook of Proton NMR Spectra

3.15

3.95

-OH

D2O

Aromatic Protons The aromatic chemical shifts of the sulfonic acid salts are similar to those of the parent acids. The shifts of benzenesulfonic acid, sodium salt are listed below followed by those of several para substituted derivatives

Benzenesulfonic acid, sodium salt

δ

b

(ppm)

δ

7.4-7.7

a

Solvent

(ppm) 7.92

-SO3-Na

D2O

Para substituted benzenesulfonic acid salts

X-

δ

b

(ppm)

δ

a

(ppm)

Solvent

H2N-

6.79

7.62

-SO3-Na

D2O

HO-

6.80

7.72

-SO3-K

D2O

R14-

7.06

7.67

-SO3-Na

7.10

7.91

-SO3-Na

D2O

CH3-

7.28

7.81

-SO3-NH4

D2O

Cl-

7.45

7.83

-SO3-Na

D2O

Br-

7.68

7.79

-SO3-Na

D2O

7.88

7.88

-SO3-Na

D2O

8.09

8.09

-SO3-K

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D2O

D2O

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Esters of Sulfonic Acid

The sulfonic acid functional group produces two distinct sets of chemical shifts for the adjacent aliphatic groups. The groups bonded to the acid side of the linkage are weakly deshielded but those bonded to the alcohol side are very strongly deshielded. This situation is analogous to that which is encountered with the esters of carboxylic acids. The sulfonic acid esters, unlike the free acids and their salts, are readily soluble in CDCI3 and CCI4, and relatively insoluble in deuterium oxide.

Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

1.39

δ

a

(ppm)

Compound

Solvent

2.94

CCI4

3.00

CDCI3

3.09

CCI4

3.85

CCI4

3.89

CDCI3

4.01

CCI4

1.25

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1.39

0.89

4.21

CCI4

3.99

CDCI3

3.71

CCI4

1.59

0.89

1.91

Aromatic Protons In relation to the aromatic hydrogens, the effect of the sulfonic acid ester linkage is opposite to that observed for the aliphatic groups, i.e. the oxygen side of the linkage weakly shields the ortho protons while the sulfur side strongly deshields them.

δ

δ

a

-X

(ppm)

Solvent

6.9-7.5

CDCl3

7.0-7.5

CCI4

b

(ppm)

7.3-7.7

δ

a

(ppm)

7.83

-X

Solvent CDCl3

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Esters of Sulfurous Acid

The esters of sulfurous acid are a small group of compounds for which only a few aliphatic derivatives are available commercially. As with all of the esters, the oxygen atom adjacent to the alpha carbon group has a strong deshielding effect upon the protons bonded to it.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

1.34

0.96 0.92

1.67

(1.2-2.0)

δ

a

(ppm)

X

Solvent

3.59

CCI4

4.04

CCI4

3.92

CDCI3

3.94

CCI4

Coupling and Coupling Constants No unusual couplings nor coupling constants have been noted for the esters of sulfurous acid. The aliphatic patterns are similar in appearance to those of similarly strong deshielding groups such as the ether group.

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The Sadtler Handbook of Proton NMR Spectra

The sulfites are readily soluble in the chlorinated solvents such as carbon tetrachloride and deutero-chloroform.

Characterization Because of the relatively narrow range of chemical shifts observed for the esters of the various sulfur containing acids, the functional group of such compounds is best characterized through the analysis of their infrared spectra.

δ

a

(ppm)

Compound

Acid

Solvent

3.59

Sulfurous acid

CCI4

3.73

Sulfuric acid

D2O

3.73

Benzenesulfonic acid

CDCI3

3.88

Methanesulfonic acid

CCI4

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Salts of Sulfuric Acid

The mono-salts of sulfuric acid display a strong deshielding effect on the aliphatic groups of the ester portion of the molecule. This deshielding effect is similar to that noted for the esters of Sulfurous acid.

Aliphatic Protons Methyl Esters

δ

δ

c

a

-X

(ppm)

Solvent

3.71

D2O

3.72

D2O

3.73

D2O

3.95

TFA

(ppm)

δ

b

(ppm)

δ

a

(ppm)

3.73

Compound CH3-O-S(O2)-O-K

Solvent D2O

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1.31

4.12

CH3-CH2-O-S(O2)-O-K

Polysol

(1.1-1.6)2

1.69

4.06

CH3(CH2)2-CH2-CH2-O-S(O2)-O-Na

D2O

(1.1-1.5)5

1.61

4.01

CH3(CH2)5-CH2-CH2-O-S(O2)-O-Na

D2O

(1.1-1.5)7

1.61

3.46

CH3(CH2)7-CH2-CH2-O-S(O2)-O-Na

Polysol

(1.1-1.6)11

1.61

3.82

CH3(CH2)1O-CH2-CH2-O-S(O2)-O-Na

Polysol

Solubility and Solvent Effects The presence of the mono-salt function makes the mono-esters much more soluble in solvents such as Polysol, DMSO-d6 and D2O than the corresponding diesters. The rather wide divergence in chemical shift noted for the compounds examined in Polysol solution most probably arises from the varying amounts of H2O which are often present in such solutions. Based upon the information supplied in the table above, it can be inferred that the chemical shifts of the sulfuric acid ester/salts appear at highest field in relatively dry Polysol solution shifting to lower field as the amount of H2O increases and finally reach maximum deshielding when the solvent is 1OO% H2O (D2O).

Diesters of Sulfuric Acid

The diesters of sulfuric acid exhibit chemical shifts similar to those of the ester/salts with minor variations due to the different solvents employed. The diesters are found to be much more soluble in the chlorinated hydrocarbons than the more polar ester/salts.

Aliphatic Protons

δ (ppm) c

1.00

δ (ppm) b

δ (ppm) a

Compound

Solvent

3.87

CCI4

1.45

4.28

CCI4

1.75

4.15

CCI4

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Chlorinated Sulfate Esters

δ (ppm) b

δ (ppm) a

3.80

4.52

CDCI3

5.79

CCI4

Compound

Solvent

Coupling and Coupling Constants The diesters of sulfuric acid do not display any additional or different couplings from the protons of the other normal aliphatic groups. Vicinal coupling is observed (JHC-CH = 6-8 Hz), but longer range coupling if present is too small in magnitude to be detected.

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Thioamides

The Thioamide functional group is interesting in that a wide variety of chemical shifts may be observed depending upon the substituents and the side of the group to which they are bonded. Non-equivalence is commonly observed for the primary amide protons and also in the case in which two different groups are bonded to the tertiary amide nitrogen atom. The thioamides tend to be less soluble in the chlorinated solvents than most of the sulfur-containing groups but are usually quite soluble in Polysol or DMSO-d6.

Aliphatic Protons

δ

a

(ppm)

2.40

Compound

Solvent DMSO-d6

CDCI3 2.62

CDCI3 3.13

CDCI3 (3.27, 3.30)

CDCI3 (3.31, 3.48)

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CDCI3 3.34

Aromatic Protons The Thioamide carbon of this functional group has a moderately strong deshielding effect on the ortho aromatic hydrogens. They appear as a distorted doubletof-doublets near 7.85 ppm while the para and meta protons produce a complex, higher order band at higher field.

Compound

δ

b

7.81

7.89

(ppm)

δ

a

(ppm)

7.3-7.6

7.1-7.5

Exchangeable Protons The Thioamide protons usually appear as very broad bands at low field. They are often non-equivalent and thus may appear separated in chemical shift by 1-2 ppm.

δ

a

-X

(ppm)

ca. 8.45

9.20

Solvent Polysol

-CH3

9.32, 9.65

DMSO-d6 DMSO-d6

Thioformaldehyde Protons The Thioformaldehyde protons resonate at very low field as a sharp to slightly broadened single peak. If the nitrogen atom is substituted by two different groups, it is possible for two stable forms to exist in which one group is syn to the aldehydic proton and the other group anti, and vice versa. Clear coupling between the aldehydic proton and aliphatic groups bonded to the nitrogen atom is usually not observed.

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The Sadtler Handbook of Proton NMR Spectra

δ

a

(ppm)

-X

Solvent

9.19

CDCI3

9.32, 9.46

CDCI3

9.53

CDCI3

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Thioureas

The Thioureas have a moderately strong deshielding effect on adjacent aliphatic groups and they usually display clear coupling to them in the case of the secondary thiourea linkage (J = 4-5 Hz). The presence of the C(=S) thiocarbonyl group greatly reduces the shielding effect of the NH group on ortho aromatic hydrogens in comparison to the effect noted for the secondary amines. The chemical shift of the various NH hydrogens varies widely depending primarily on the type of sub-stitution present in the molecule. In the case of the primary thiourea protons, the two hydrogens bonded to the nitrogen atom may be nonequivalent leading to different chemical shifts for each proton.

Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent

2.80

DMSO-d6

(3.29)

Poly so I

3.28

DMSO-d6

3.52)

CDCI3

1.04

(1.20

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The Sadtler Handbook of Proton NMR Spectra

3.52

CCI4

3.66

CDCI3

3.61)

Polysol

4.32

CDCI3

3.30

Polysol

1.22

1.19

(0.92

1.64

(1.24)

(0.95)

1.92

Aromatic Protons The aromatic protons bonded to the nitrogen nuclei of the thiourea group are neither strongly shielded nor deshielded. They appear in the spectrum as a complex band in the chemical shift range from about 6.9 to 7.7 ppm. The shape and complexity of this higher order pattern is quite sensitive to the presence and type of other substituents bonded to the thiourea linkage.

Thiourea substituted phenyl groups

(ppm) a 6.90-7.60

Compound

Solvent

δ

DMSO-d6

7.00-7.70

CDCI3

7.10-7.60

DMSO

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The Sadtler Handbook of Proton NMR Spectra

Exchangeable Protons Although the chemical shifts of the exchangeable protons of the thioureas vary markedly with solvent, temperature and the presence of H2O in solution, the tables below indicate a trend in shift with the type of substitution of the thiourea nitrogen atoms. It is noted that the primary amide protons resonate at highest field (H2N-C(=S)-), that alkyl substituted secondary amide protons resonate at slightly lower field (R-NH-C(=S)-), and that the phenyl substituted secondary

.

groups resonate at lowest field

δ

-X

(ppm) a 5.0-8.0

Solvent

-NH-CH3

DMSO-d6

6.31

Polysol

6.88

DMSO-d6

6.93

-NH-R2

DMSO-d6

7.00

Polysol

7.11

-NH2

DMSO

7.32

DMSO-d6

-X

δ

a

(ppm)

6.10

R2-

-Y

Solvent

-NH-R

CDCI3

6.19

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CDCI3

The Sadtler Handbook of Proton NMR Spectra

R2-

6.67

-NH-R2

CCI4

R10-

7.10

-NH-R 10

CH3-

7.50

-NH2

DMSO-d6

R2-

7.50

-NH2

DMSO-d6

Polysol

7.97

CDCI3

8.04

CDCI3

8.62

-NH-R2

CDCI3

Polysol

9.13

9.57

-NH2

Polysol

9.66

-NH2

DMSO-d6

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Sulfonamides

The Sulfonamides produce two distinct sets of chemical shifts. The protons of hydrocarbon groups bonded to the nitrogen side of the linkage resonate at higher field than the corresponding protons of groups bonded to the SO2 side. In addition to the characteristic chemical shifts thus produced, the sulfonamides usually display clear coupling between an aliphatic group and the NH proton adjacent to it. These compounds are generally more soluble in DMSO-d6 and Polysol than in the chlorinated solvents. There appears to be a distinct deshielding of the NH protons in DMSO-d6 and Polysol in comparison to similar protons in CDCl3.

Aliphatic Protons

δ b (ppm)

δ

a

(ppm)

Compound

2.60

Solvent Polysol

(2.69)

CDCI3

(2.83)

CDCI3

(2.85)

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

1.08

2.97

(1.13)

DMSO-d6

Polysol

3.40

(1.20)

δ

b

(ppm)

CDCI3

δ

a

(ppm) 2.78

Compound

Solvent CDCI3

3.00

3.03

CDCI3

Polysol

1.33

3.10

CDCI3

1.40

3.18

CDCI3

1.40

3.47

CDCI3

Aromatic Protons The SO2 side of the sulfonamide linkage is a strong deshielding group in its effect on the ortho aromatic hydrogens. These protons usually resonate in the range from 7.5-7.9 ppm. The nitrogen side of the sulfonamide group is a weakly shielding substituent on all the aromatic protons and they appear as a broad single peak near 7.1 ppm.

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The Sadtler Handbook of Proton NMR Spectra

Compound

δ

a

Solvent

(ppm)

ca. 7.12

CDCI3

7.87, 7.5-7.8

DMSO-d6

Para Substituted Sulfonamides

δ

b

(ppm)

δ

a

(ppm)

para

Solvent Poly so I

7.19

6.88

-CH3 6.95

R-SO2-NH-

6.95

6.98

7.09

7.21

7.2

7.01

7.01

CDCI3

-R2

TFA

-Cl

DMSO-d6

-Br

CDCI3

-I

Acetone

7.31

7.54

Poly so I 7.26

7.73

7.40

8.03

Acetone

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The Sadtler Handbook of Proton NMR Spectra

δ

b

(ppm)

δ

a

-X

(ppm)

Solvent

7.50

6.64

-NH2

DMSO-d6

7.75

6.98

-O-CH3

Poly so I

8.07

7.37

-F

Acetone

7.90

7.57

-Cl

Acetone Polysol

7.89

7.89

7.99

8.11

8.10

8.43

Polysol

-NO2

DMSO-d6

Exchangeable Protons Primary Sulfonamides

δ 5.24

a

-X

(ppm) -R2

Solvent CDCI3

6.50

Polysol

6.89

DMSO-d6

7.11

Poly so I

7.11

DMSO-d6

7.21

DMSO-d6

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The Sadtler Handbook of Proton NMR Spectra

Coupling and Coupling Constants Coupling between aliphatic groups and the adjacent NH proton is usually observed. The coupling constant is similar in magnitude to normal vicinal CH-CH coupling, JCH—NH = 6-8 Hz

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Aliphatic and Olefinic Ethers

Because the compounds containing an ether linkage are of such commercial importance and because such a large number of compounds are available, the chemical shifts of this group have been divided into five separate sections; Aliphatic and Olefinic, Alicyclic, Aromatic, Heterocyclic and, the Silicon and Phosphorus Ethers.

Aliphatic Protons The aliphatic groups bonded to the ether linkage are moderately strongly deshielded. In addition, the aliphatic groups bonded to an olefinic ether linkage are more strongly deshielded than those of an aliphatic ether substituent.

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

(ppm) a 3.11

Compound CCI4

3.22

CH3-O-R5

CCI4

3.30

CH3-O-R4

CDCI3

3.72

0.93

Solvent

CCI4

1.13

3.38

CH3-CH2-O-R2

CCI4

1.23

3.71

1.60

3.37

CH3-CH2-O-CH=CH-CH3

CCI4

(1.12)

3.51

CCI4

CH3-CH2-CH2-O-R3

CDCI3

0.91

(1.1-1.8)

(1.1-1.8)

3.37

CDCI3

0.91

(1.1-1.8)

(1.1-1.8)

3.60

CCI4

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The Sadtler Handbook of Proton NMR Spectra

1.80

3.09

CCI4

1.90

3.38

CCI4

(0.89)

(0.97)

(1.12)

CCI4

Substituted Methyl Ethers

δ

b

(ppm)

δ

a

X

(ppm)

Solvent

3.30

3.37

-R3

CDCI3

3.43

3.89

CDCI3

3.38

3.90

CCI4

3.30

3.99

3.47

4.02

3.46

4.14

3.49

4.30

CCI4

3.29

4.35

CDCI3

3.23

4.40

CCI4

-C≡C-H

CDCI3

CCI4

-C≡N

-O-CH3

CDCI3

Substituted Methyl Ethyl Ethers

δ

c

(ppm)

3.38

δ

b

(ppm)

3.54

δ

a

X

(ppm)

2.52

-C≡N

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Solvent CC!4

The Sadtler Handbook of Proton NMR Spectra

CDCI3 3.26

3.53

2.73

3.37

3.42

2.86

-NH2

3.39

3.65

3.40

-Br

CCI4

3.38

3.51

3.71

-OH

CDCI3

CDCI3

Olefinic Protons In regard to the vinyl protons, the ether linkage is a strongly deshielding substituent in its effect on the chemical shift of the proton attached to the alpha carbon (the geminal hydrogen), but is a strong shielding group in its effect on the cis and trans protons.

Vinyl Ethers

cis (ppm)

trans (ppm)

geminal (ppm)

-R

4.01

3.84

6.32

-O-R4

4.08

3.89

6.35

Solvent CC!4 CC!4

Substituted Vinyl Ethers

δ

b

(ppm)

δ

a

-X

(ppm)

Solvent

5.82

4.27

-CH3

(cis)

CCI4

6.12

4.68

-CH3

(trans)

CCI4 CDC!3

7.54

5.42

7.50

5.52

CCI4

Polysol 7.76

6.68

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The Sadtler Handbook of Proton NMR Spectra

Poly so I 7.79

6.72

Vinyl Coupling and Coupling Constants Because of the clear separation in chemical shifts produced by ether substituents on the vinyl protons, the various coupling constants are often clearly displayed.

J values Geminal

J

Cis

J H-C=C-H

=

7.0 Hz

Trans

J

=

14.5 Hz

Geminal

J CH3-C-H

=

6.9 Hz

Cis

J CH3-C=C-H

Trans

J CH3-C=C-H

H2C=C

H-C=C-H

=

1.7 Hz

=

1.6 Hz =

1.6 Hz

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Alicyclic Ethers

The broadening of multiplets due to the lack of rotation about the carbon-carbon bonds of the protons in the ring and the absence of terminal methyl groups are often sufficient evidence to characterize the HNMR spectra of the alicyclic compounds. The cyclic ethers are all readily soluble in the chlorinated solvents CCl4 and CDCI3. The three ring protons of the epoxide group are non-equivalent and appear as three distinct multiplets in the chemical shift range from 2.3 to 3.8 ppm delta. The two protons bonded to C-1 resonate at higher field than the proton attached to C-2. The appearance and chemical shifts of these bands are readily recognizable and quite characteristic of this group.

δ

e

(ppm)

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ a (ppm)

4.62

3.71

3.56

1.59

2.64

4.62

1.81

3.71

Compound

Solvent CCI4 CDCI3

1.81

1.59

CCI4 1.59

3.56

Epoxy Ring Protons

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The Sadtler Handbook of Proton NMR Spectra

cis δ

c

(ppm)

trans δ

b

(ppm)

δ

a

X

(ppm)

Solvent

2.31

2.55

2.69

-R2

CCI4

2.28

2.56

2.74

-R10

CCI4

2.23

2.59

2.80

-CH3

CCI4

2.46

2.63

2.98

-CH2-O-R

CCI4

2.58

2.79

3.17

-CH2-CI

CCI4

2.60

2.90

3.30

-CH=CH2

CDCI3

2.58

2.84

3.40

-CH2-Br

CCI4

2.61

2.96

3.69

CCI4

Coupling and Coupling Constants Due to the high degree of strain in the three membered ring, the coupling constants between the three hydrogens of the epoxide group are observed to be somewhat smaller than normally expected. The coupling constants can be J = 5, 4 and 3 Hz for the geminal, cis and trans couplings.

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Aromatic Ethers

The HNMR spectra of the phenyl ethers are often easily characterized by means of the low field shifts observed for aliphatic groups bonded to the phenoxy moiety and from the high field shifts observed for the ortho and para protons. The compounds are normally soluble in CCI4, CDCI3 and DMSO-d6. The spectra of the aromatic ethers possess no unusual features with the exception of the chemical shifts noted.

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent

3.70

CCI4

1.31

3.89

CCI4

1.71

3.85

CDCI3

1.70

3.87

CCI4

0.90

0.99 1.45

1-Substituted Methyl Phenyl Ethers

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The Sadtler Handbook of Proton NMR Spectra

δ

a

(ppm)

3.89

-X

Solvent

-CH3

CCI4 CCI4

4.36

CDCI3 4.47

CCI4 4.80

4.81

-c≡c-h

DMSO-d6

4.92

-C≡n

CDCI3 CDCI3

5.18

2-Substituted Methyl Phenyl Ethers

δ

b

(ppm)

δ

a

(ppm)

-X -CH3

Solvent

3.85

1.71

CDCI3

4.21

2.79

3.89

2.99

-NH2

CDCI3

4.19

3.52

-Br

CDCI3

4.00

3.59

-O-CH3

CCI4

4.05

3.63

-Cl

CCI4

4.06

4.29

CDCI3

CCI4

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The Sadtler Handbook of Proton NMR Spectra

4.08

4.39

CDCI3

Aromatic Protons Methyl Phenyl Ether

δ

c

(ppm)

δ

b

6.78

(ppm)

δ

7.19

a

Solvent

(ppm)

6.80

CCI4

Diphenyl Ether

(ppm)

Solvent

6.78-7.40

CCI4

Para Substituted Methyl Phenyl Ethers

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

3.75

6.79

6.79

3.71

6.79

6.79

3.71

6.80

6.90

-X

Solvent CDCI3

-O-CH3

CDCI3

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

3.61

6.65

7.08

-CH=CH-CH3

CCI4

3.77

6.79

7.09

-CH3

3.70

6.72

7.18

-Cl

CCI4

3.71

6.69

7.29

-Br

CCI4

3.76

6.81

7.30

-SH

CDCI3

3.76

6.93

7.49

3.74

6.68

7.53

3.65

6.81

7.73

CDCI3

CDCI3

-I

CDCI3 CDCI3

CDCI3 3.79

6.91

7.79

3.89

6.91

8.12

CCI4

Para Substituted Diphenyl Ethers

δ

(ppm) b 6.85

δ

a

(ppm)

-X

Solvent

6.55

-NH2

CDCI3

6.91

6.77

-OH

CDCI3

6.90

6.80

-O-CH3

CDCI3

6.75

7.29

-Br

CCI4

7.02

7.39

-Cl

CDCI3

7.03

7.80

CDCI3

6.98

8.07

CDCI3

7.10

8.27

CCI4

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Furans

Furan and its derivatives are the major heteroaromatic group of the ether compounds. Their NMR spectra display characteristic chemical shifts and coupling constants producing spin-spin coupling patterns similar to those of the pyrroles and thiophenes. The oxygen atom in the ring strongly deshields the hydrogens on the adjacent carbons (C-2 and C-5) but shields the protons bonded to positions C-3 and C-4.

δ (ppm) d

δ (ppm) c

7.37

6.30

δ

b

(ppm)

δ

a

6.30

(ppm)

Solvent

7.37

CCl4

-X

Solvent

2-Substituted Furans

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

6.85

6.23

5.11

-O-CH3

7.15

6.13

5.83

-CH3

7.30

6.25

6.14

-CH2-SH

7.82

7.29

6.67

7.59

6.58

6.92

7.64

6.59

7.05

CDCI3 CCI4 CDCI3 DMSO-d6

-CH=CH-NO2

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CDCI3 D2O

The Sadtler Handbook of Proton NMR Spectra

7.60

6.55

7.11

7.82

6.70

7.52

-C≡N

CCI4 CCI4

Coupling and Coupling Constants The furan coupling constants are much smaller in magnitude than the corresponding ortho and meta coupling constants of the benzene derivatives. It is characteristic of the furans and the other heteroaromatic compounds that the "ortho" couplings, J2-3 and J3-4 are not the same. J 2-3 = 1.7-2.0 Hz J J

3-4 = 3.0-4.0 Hz 2-4 = 0.7-1.0 Hz

Solubility and Solvent Effects Excluding the solubility limitations imposed by the substituents that may be bonded to the furan ring system, the compounds are readily soluble in the chlorinated solvents normally utilized as NMR solvents (CCI4 and CDCI3).

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Silicon Ethers

The HNMR spectra of the silicon ethers appear quite similar to those of the aliphatic ethers. The presence of the silicon nucleus can normally be detected only when a hydrocarbon group is bonded directly to it. The silicon ethers are readily soluble in carbon tetrachloride and deuterochloroform.

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

-X

Solvent

3.52

CCI4

3.56

CCI4

3.57

CDCI3

3.59

CCI4

3.77

CCI4

1.13

1.20

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The Sadtler Handbook of Proton NMR Spectra

3.81

CDCI3

4.17

CCI4

4.21

CCI4

3.71

CCI4

1.22

1.15

1.17

0.94 1.35

1.55

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Phosphorus Ethers

The esters of phosphorus acid (P- (O-R)3) possess chemical shifts characteristic of the oxygen substituent and in addition display additional coupling across the oxygen linkage to the phosphorus atom. This coupling to the first aliphatic group is usually similar to that of three bond proton-proton coupling (J = 6-8 Hz). The magnitude of the coupling constant between phosphorus atom and the second aliphatic group is usually too small to be clearly observed.

Aliphatic Protons

δ

b

(ppm)

δ

a

X

(ppm)

1.21

Solvent

3.41

CCl4

3.80

CCl4

Aromatic Protons Triphenyl Phosphite

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(ppm)

Solvent

6.90-7-50

CDCl3

δ

a

Coupling and Coupling Constants J P-O-CH2 = 6.8 Hz J

P-O-C-CH3 = 0-1 Hz

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Primary Alcohols Aliphatics

The primary alcohols characteristically produce HNMR spectra containing a methylene group in the chemical shift range from 3.3 to 5.4 ppm and one exchangeable proton which normally resonates over the range from 1.0 to 6.0 ppm. Both groups may be significantly broadened by partial coupling with each other. This coupling and the attendant broadening is easily eliminated by the addition of either acid or D2O to the sample solution.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

(0.95)

(ppm)

δ

a

(ppm)

-X

Solvent

3.34

CH3-OH CCI4

1.17

3.58

CH3-CH2-OH CCI4

0.94

1.49

3.50

(0.89)

1.67

3.27

CH3-CH2-CH2-OH CCI4 CCI4

3.20

CCI4

(0.87)

0.91

b

1.35

1.55

3.52

1.50

3.71

CH3-CH2-CH2-CH2-OH CCI4 CDCI3

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(0.91)

1.38

1.72

3.52

CCI4

The Hydroxy Group As with the other exchangeable protons, the chemical shift of the hydroxyl groups varies with concentration, temperature, solvent and the presence of impurities such as acid, base of H2O. The trend for hydroxyl groups to resonate at a lower field as their concentration in solution increases, can be illustrated by the selection of straight chain alcohols listed below. Note that as the molecular weight of the compound decreases with decreasing chain length, the chemical shift of the hydroxyl resonance increases proportionately.

δ

HO (ppm)

-X

1.62

-R20

CDCI3

2.05

-R18

CDCI3

3.24

-R11

CCI4

3.67

-R6

CCI4

4.11

-R4

CCI4

4.40

-R2

CCI4

b

(ppm)

δ

a

Solvent

-X

(ppm)

Solvent

3.49

3.07

PolysolI

3.48

3.32

CCI4

4.40

3.58

-CH3

CCI4

3.62

-(CH2-OH)3

D2O

4.46

3.90

-CF3

CDCI3

4.11

3.92

-CH=CH-CH3

CC!4

4.60

4.05

-CH=CH2

4.06

CC!4 D2O

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The Sadtler Handbook of Proton NMR Spectra

3.76

4.07

CCI4

3.99

4.11

-C≡C-CH3

CCI4

4.01

4.23

-C≡C-H

CDCI3

3.80

4.27

CDCI3

4.29

D2O

4.41

CCI4

4.46

D2O

3.32

4.50

CDCI3

4.45

4.61

CDCI3

6.27

4.71

CDCI3

5.02

4.78

CDCI3

3.63

4.86

3.10

CDCI3

2-Substituted Ethanols

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

-X

Solvent

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The Sadtler Handbook of Proton NMR Spectra

3.71

3.50

1.49

-CH3

3.45

2.50

2.57

3.65

2.37

-CH=CH2

CDCI3

3.67

3.67

2.38

-C≡C-H

CCI4

3.99

3.80

2.58

-C≡N

CDCI3

3.69

2.68

-SH

D2O

3.54

2.73

-NH2

CDCI3

3.71

2.77

3.52

2.82

CCI4

CCI4

CDCI3

2.44

3.41

CCI4 3.69

3.01

3.93

3.12

-SO-K

D2O

3.85

3.18

-NH2 (HCI)

D2O

4.29

3.85

3.45

-Br

CCI4

2.49

3..71

3.51

-O-CH3

4.61

4.05

3.56

4.50

3.79

3.63

CDCI3 CDCI3

-Cl

CDCI3

Coupling and Coupling Constants Clearly defined coupling between the hydroxyl group and the adjacent hydrocarbon group is usually not observed in solutions of the alcohols in CCI4 and CDCI3. It appears that in these solvents, the hydroxyl protons are exchanging at an intermediate rate resulting in a broadening of both resonance bands. Sometimes a relatively clear coupling is observed (J CH2-OH = 5 Hz) indicating a much slower rate of exchange. In solutions of alcohols in acetone and DMSO, clear coupling between the hydroxyl protons and adjacent hydrocarbon groups is the rule rather than the exception and it appears to result from the presence of the small amount of water that is usually present in these solvents. The addition of a small amount of D2O or acid will remove any coupling or broadening that appears in the HNMR spectra of the alcohols. The exchange rate can be increased by heating the sample solutions, resulting in sharp single peaks for the hydroxyl resonance. The hydroxyl protons often interchange with other types of exchangeable protons present in the same molecular structure.

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Primary Alcohols Olefinics

The primary alcohols characteristically produce HNMR spectra containing a methylene group in the chemical shift range from 3.3 to 5.4 ppm and one exchangeable proton which normally resonates over the range from 1.0 to 6.0 ppm. Both groups may be significantly broadened by partial coupling with each other. This coupling and the attendant broadening is easily eliminated by the addition of either acid or D2O to the sample solution.

The Hydroxy Group As with the other exchangeable protons, the chemical shift of the hydroxyl groups varies with concentration, temperature, solvent and the presence of impurities such as acid, base of H2O. The trend for hydroxyl groups to resonate at a lower field as their concentration in solution increases, can be illustrated by the selection of straight chain alcohols listed below. Note that as the molecular weight of the compound decreases with decreasing chain length, the chemical shift of the hydroxyl resonance increases proportionately.

HO (ppm)

-X

Solvent

1.62

-R20

CDCI3

2.05

-R18

CDCI3

3.24

-R11

CCI4

3.67

-R6

CCI4

4.11

-R4

CCI4

4.40

-R2

CCI4

Coupling and Coupling Constants Clearly defined coupling between the hydroxyl group and the adjacent hydrocarbon group is usually not observed in solutions of the alcohols in CCI4 and CDCI3. It appears that in these solvents, the hydroxyl protons are exchanging at an intermediate rate resulting in a broadening of both resonance bands. Sometimes a relatively clear coupling is observed (J CH2-OH = 5 Hz) indicating a much slower rate of exchange.

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The Sadtler Handbook of Proton NMR Spectra

In solutions of alcohols in acetone and DMSO, clear coupling between the hydroxyl protons and adjacent hydrocarbon groups is the rule rather than the exception and it appears to result from the presence of the small amount of water that is usually present in these solvents. The addition of a small amount of D2O or acid will remove any coupling or broadening that appears in the HNMR spectra of the alcohols. The exchange rate can be increased by heating the sample solutions, resulting in sharp single peaks for the hydroxyl resonance. The hydroxyl protons often interchange with other types of exchangeable protons present in the same molecular structure.

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Primary Alcohols Aromatics

The primary alcohols characteristically produce HNMR spectra containing a methylene group in the chemical shift range from 3.3 to 5.4 ppm and one exchangeable proton which normally resonates over the range from 1.0 to 6.0 ppm. Both groups may be significantly broadened by partial coupling with each other. This coupling and the attendant broadening is easily eliminated by the addition of either acid or D2O to the sample solution.

The Hydroxy Group As with the other exchangeable protons, the chemical shift of the hydroxyl groups varies with concentration, temperature, solvent and the presence of impurities such as acid, base of H2O. The trend for hydroxyl groups to resonate at a lower field as their concentration in solution increases, can be illustrated by the selection of straight chain alcohols listed below. Note that as the molecular weight of the compound decreases with decreasing chain length, the chemical shift of the hydroxyl resonance increases proportionately.

HO (ppm)

-X

Solvent

1.62

-R20

CDCI3

2.05

-R18

CDCI3

3.24

-R11

CCI4

3.67

-R6

CCI4

4.11

-R4

CCI4

4.40

-R2

CCI4

Coupling and Coupling Constants Clearly defined coupling between the hydroxyl group and the adjacent hydrocarbon group is usually not observed in solutions of the alcohols in CCI4 and CDCI3. It appears that in these solvents, the hydroxyl protons are exchanging at an intermediate rate resulting in a broadening of both resonance bands. Sometimes a relatively clear coupling is observed (J CH2-OH = 5 Hz) indicating a much slower rate of exchange.

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The Sadtler Handbook of Proton NMR Spectra

In solutions of alcohols in acetone and DMSO, clear coupling between the hydroxyl protons and adjacent hydrocarbon groups is the rule rather than the exception and it appears to result from the presence of the small amount of water that is usually present in these solvents. The addition of a small amount of D2O or acid will remove any coupling or broadening that appears in the HNMR spectra of the alcohols. The exchange rate can be increased by heating the sample solutions, resulting in sharp single peaks for the hydroxyl resonance. The hydroxyl protons often interchange with other types of exchangeable protons present in the same molecular structure.

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Secondary Alcohols

The methine proton adjacent to the hydroxyl group of the secondary alcohols is very strongely deshielded and may appear as any of a wide variety of multiplets depending upon the aliphatic groups bonded to it. The highest degree of multiplicity that is observed is octet produced by the two methyl groups of isopropanol with additional coupling to the hydroxyl group.

Aliphatic Protons

δ

d

(ppm)

(ppm)

δ c

(ppm)

δ b

(ppm)

δ a

-X

Solvent CCI

(1.29)

3.99

CCI

(0.90 1.9)

3.36

4

2.90

4

3.30

(0.92

CDCI

1.62)

3.01

1.64

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3

The Sadtler Handbook of Proton NMR Spectra

CCI

5.59

4

2.28

CDCI (3.59)

4.03

3.27

Alicyclic Protons

(CH2)n (ppm)

(ppm)

δ

(ppm)

δ

b

a

1.1-2.5

4.16

5.48

1.3-2.1

4.21

3.58

Compound

Solvent CCI 4 CCI 4

CCI 4 0.8-2.5

3.49

4.20

CDCI 1.2-2.3

3.80

2.69

Disubstituted Methanols

(ppm)

δ b

(ppm)

δ a

X(Y)(

Solvent CDCI

2.77

3.11

CCI 1.95

3.18

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3

4

3

3

The Sadtler Handbook of Proton NMR Spectra

CCI 2.59

4

3.38

CCI 4 3.05

3.43

2.90

3.99

CCI 4

CCI 4 3.63

4.03

CCI 4 3.88

4.20

CDCI 3.73

3

4.22

CDCI 3.41

3

4.30

D2O 4.40

4.08

4.50

4.05

4.60

CCI 4

CDCI

3

CCI 4 2.76

4.65

D2O

4.94

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CDCI

4.60

3

5.91

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Secondary Alcohols

The methine proton adjacent to the hydroxyl group of the secondary alcohols is very strongely deshielded and may appear as any of a wide variety of multiplets depending upon the aliphatic groups bonded to it. The highest degree of multiplicity that is observed is octet produced by the two methyl groups of isopropanol with additional coupling to the hydroxyl group.

Aliphatic Protons

δ

d

(ppm)

(ppm)

δ c

(ppm)

δ b

(ppm)

δ a

-X

Solvent CCI

(1.29)

3.99

CCI

(0.90 1.9)

3.36

4

2.90

4

3.30

(0.92

CDCI

1.62)

3.01

1.64

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The Sadtler Handbook of Proton NMR Spectra

CCI

5.59

4

2.28

CDCI (3.59)

4.03

3.27

Alicyclic Protons

(CH2)n (ppm)

(ppm)

δ

(ppm)

δ

b

a

1.1-2.5

4.16

5.48

1.3-2.1

4.21

3.58

Compound

Solvent CCI 4 CCI 4

CCI 4 0.8-2.5

3.49

4.20

CDCI 1.2-2.3

3.80

2.69

Disubstituted Methanols

(ppm)

δ b

(ppm)

δ a

X(Y)(

Solvent CDCI

2.77

3.11

CCI 1.95

3.18

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3

4

3

3

The Sadtler Handbook of Proton NMR Spectra

CCI 2.59

4

3.38

CCI 4 3.05

3.43

2.90

3.99

CCI 4

CCI 4 3.63

4.03

CCI 4 3.88

4.20

CDCI 3.73

3

4.22

CDCI 3.41

3

4.30

D2O 4.40

4.08

4.50

4.05

4.60

CCI 4

CDCI

3

CCI 4 2.76

4.65

D2O

4.94

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CDCI

4.60

3

5.91

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Tertiary Alcohols

The tertiary alcohols are a difficult group of compounds to identify using only their NMR spectra. Their most characteristic feature is the presence of a single exchangeable proton which does not display any couplings since there are no protons on the adjacent carbon atom. The phenols will be treated as a separate group. The series of 1-substituted-2-propanols listed below illustrates the relatively narrow range of chemical shifts (less than 1 ppm) that is observed for the hydrocarbon groups of the tertiary alcohols.

Aliphatic Protons 1-Substituted-2-propanols

δ

b

(ppm)

δ

a

(ppm)

-X

Solvent

2.89

1.15

-R2

CCI4

1.40

1.18

-R3

CCI4

2.40

1.20

-CH3

CCI4

2.14

1.23

-CH=CH2

2.34

1.51

2.30

1.53

-c≡c-h

1.54

-SO2-O-Na

CCI4 CDCI3

CDCI3 D2O

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The Sadtler Handbook of Proton NMR Spectra

3.49

1.61

2.62

1.77

-C≡N

CDCI3 CDCI3

Coupling and Coupling Constants The coupling constants between protons on adjacent carbons (CH-CH) are similar to those of the corresponding structures of other types of substituents. Because none of the hydrocarbon groups are strongly deshielded by the hydroxyl group, complex higher order patterns at high field are to be expected.

Solubility and Solvent Effects Except for compounds containing water soluble groups such as the sodium and potassium salts of organic acids, the simple tertiary alcohols are normally soluble in the chlorinated solvents, CCI4 and CDCI3. The use of hydroscopic solvents such as acetone and DMSO should be avoided whenever possible because the relatively weak hydroxyl resonance may exchange with water in the solvent and its presence could go undetected.

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Tertiary Alcohols

The tertiary alcohols are a difficult group of compounds to identify using only their NMR spectra. Their most characteristic feature is the presence of a single exchangeable proton which does not display any couplings since there are no protons on the adjacent carbon atom. The phenols will be treated as a separate group. The series of 1-substituted-2-propanols listed below illustrates the relatively narrow range of chemical shifts (less than 1 ppm) that is observed for the hydrocarbon groups of the tertiary alcohols.

Coupling and Coupling Constants The coupling constants between protons on adjacent carbons (CH-CH) are similar to those of the corresponding structures of other types of substituents. Because none of the hydrocarbon groups are strongly deshielded by the hydroxyl group, complex higher order patterns at high field are to be expected.

Solubility and Solvent Effects Except for compounds containing water soluble groups such as the sodium and potassium salts of organic acids, the simple tertiary alcohols are normally soluble in the chlorinated solvents, CCI4 and CDCI3. The use of hydroscopic solvents such as acetone and DMSO should be avoided whenever possible because the relatively weak hydroxyl resonance may exchange with water in the solvent and its presence could go undetected.

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Diols and Polyols

The polyols are one of the groups of compounds for which the proton NMR integration ratios are most useful in determining their molecular structure. The polyols characteristically display the resonance of two or more exchangeable protons with three or more hydrocarbon groups resonating at low field in the range from 3 to 4 ppm. The straight chain polyols, and their cyclic counterparts, possess no methyl absorption bands at high field making their identification somewhat easier than the corresponding branched chain compounds.

1,n-Alkanediols

n δ c (ppm) δ b (ppm) δ a (ppm) 0 3.68

Solvent D2 O

1

1.78

3.65

D2O

2

1.43

3.39

3

1.2-1.9

3.60

4

1.1-1.8

3.65

4.52

CDCI3

7

1.1-1.8

3.60

3.05

CDCI3

14

ca 1.32

3.40

3.92

DMSO-d6

4.34

DMSO-d6 D2O

Coupling and Coupling Constants As with the primary and secondary alcohols, coupling between the hydroxyl group and adjacent methylene or methine groups may or may not be observed depending to a great extent on the solvent employed. In D2O solution, of course, the hydroxyl proton will be replaced by deuterium and no coupling will be observed. In acetone and dimethyl sulfoxide solutions coupling between the OH and adjacent aliphatic groups is usually clearly observed (JCH- OH = 4-6 Hz). In carbon tetrachloride and deuterochloroform solutions, the coupling across the oxygen group of the

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The Sadtler Handbook of Proton NMR Spectra

polyols is usually not observed or at most, both groups may be badly broadened.

Solubility and Solvent Effects With the exception of the very high molecular weight varieties, the polyols are readily soluble in one of the usually employed NMR solvents. The compounds containing approximately equal numbers of carbon and oxygen atoms are soluble in D2O. At ratios of about three carbons per hydroxyl group, acetone or DMSO-d6 will be found to be most effective. When the ratio of carbon to oxygen atoms exceeds 7 or 8, CDCl3 and CCI4 become more useful in dissolving such compounds con-taining large hydrocarbon fragments.

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Sugars and Carbohydrates

This specialized group of polyols characteristically displays few resonance bands at high field. Their NMR spectra usually consist of a complex higher order pattern in the chemical shift range from 3-4 ppm, with the cyclic varieties displaying one or two additional doublets at lower field (4-6 ppm). These doublets represent the axial and equatorial protons bonded to the carbon nucleus adjacent to the ether linkage of the furanosides and pyranosides. All of the carbohydrates are readily soluble in deuterium oxide although they may dissolve only slowly. Proton NMR is useful in determining the relative percentages of alpha and beta forms, but the spectra are not otherwise readily interpretable except for direct comparison of the pattern with that of a reference compound. The chemical shift data for several selected pyranosides which appear in this database are presented.

Pyranosides

CH-2,3,4,5 (ppm)

Axial (ppm)

Equatorial (ppm)

Solvent

Arabinopyranose

3.3-4.2

4.51

5.24

D2O

Glucose

3.0-4.1

4.60

5.20

D2O

Galactose

3.3-4.3

4.60

5.30

D2O

Xylose

3.1-4.2

4.68

5.28

D2O

Mannose

3.2-4.0

4.89

5.19

D2O

Coupling and Coupling Constants Three types of coupling can occur in the spectra of the cyclic sugars; axial-axial, axial-equatorial and equatorial-equatorial. Because the size of the coupling constant varies with the dihedral angle between the coupled protons, the axial-axial interaction is significantly larger than the other two types. Ranges of observed coupling constants for these three couplings are presented.

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The Sadtler Handbook of Proton NMR Spectra

J J

values

Hz

axial-axial

5-8

J axial-equatorial

1-4

J equatorial-equatorial

1-4

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Phenols

The phenolic compounds characteristically display high field chemical shifts for the aromatic hydrogens ortho and para to the hydroxyl substituent. The single hydroxyl proton resonates at much lower field than the corresponding OH group of the alcohols but at higher field than that of the carboxylic acids.

Phenol

HO- (ppm)

δ

6.11

c

(ppm)

δ

b

6.75

(ppm) 7.14

δ

a

(ppm)

Solvent

6.79

CDCI3

Para-Substituted Phenols

δ

c

(ppm)

5.77

δ

b

(ppm)

δ

a

Solvent

(ppm)

6.62

6.62

-O-CH3

CCI4

6.79

6.79

-OH

D2O

6.45

6.69

6.92

-CH3

CDCI3

6.53

6.79

6.91

-F

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

6.39

6.78

7.03

CDCI3

4.95

6.75

7.08

-C6

CDCI3

6.33

6.71

7.10

-Cl

CDCI3

4.73

6.75

7.22

-S-CH3

CDCI3

4.91

6.75

7.23

5.20

6.69

7.30

9.49

6.87

7.43

6.80

6.91

7.46

-CF3

CDCI3

5.41

6.59

7.48

-I

CDCI3

6.84

6.88

7.58

8.70

6.63

7.67

-N=O

10.50

6.93

7.72

-SO2-O

7.05

7.87

-SO2-O-Na

9.76

7.07

8.11

Acetone

9.32

7.06

8.15

Acetone

CDCI3

-Br

CDCI3 DMSO

DMSO-d6

Acetone DMSO-d6 D2O

Solubility and Solvent Effects Phenol and the simple aliphatic substituted phenols are soluble in CCl4 and CDCI3. As indicated above in the table of chemical shifts, the presence of other functional groups may require the use of D2O, Poiysol, Acetone or DMSO-d6.

Characterization The presence of an exchangeable proton band at relatively low field and the relatively high field chemical shifts produced by the hydroxyl group on the ortho and para aromatic hydrogens makes the phenols a relatively simple group of compounds to characterize.

Only the anilines, produce similar chemical shifts, however, the resonance bands of the anilines are sensitive to the addition of acid to the sample solution while the phenols are not affected in the same manner.

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Ketones Aliphatics and Alicyclics

The Ketone linkage weakly deshields the protons of adjacent aliphatic groups but strongly deshields the ortho aromatic protons. The ketones are readily soluble in carbon tetrachloride and deutero-chloroform.

Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent

2.05

CCI4

2.07

CCI4

2.11

2.20

CCI4

2.40

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

2.43

CCI4

2.29

CCI4

2.40

CCI4

2.43

CDCI3

2.94

CDCI3

2.31

CCI4

2.82

CCI4

2.50

CCI4

3.07

CCI4

3.47

CCI4

1.03

0.99

0.92

1.18

0.90

0.95

1.58

1.72

(1.05)

(1.00)

(1.18)

CCI4 (1.11)

(0.91)

2.22

CCI4

2.28

CCI4

2.00

(1.02)

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The Sadtler Handbook of Proton NMR Spectra

Alicyclic Protons

n

δ

c

(ppm)

δ

0

b

(ppm)

δ

a

Ring

(ppm)

Solvent

2.02

2.02

Cyclopentanone

CCI4

1

ca. 1.79

ca 1.79

2.25

Cyclohexanone

CCI4

2

ca. 1.71

ca 1.71

2.49

Cycloheptanone

CDCI3

3

ca. 1.47

1.82

2.31

Cyclooctanone

CCI4

8

ca. 1.29

1.62

2.36

Cyclotridecanone

CCI4

10

ca. 1.33

1.64

2.43

Cyclopentadecanone

CDCI3

Coupling and Coupling Constants No unusual couplings nor coupling constants are observed in the NMR spectra of the Ketones. The aliphatic three bond vicinal coupling JHC-CH is 6-8 Hz, the aromatic ortho coupling constant varies from 8-9 Hz, and the olefinic coupling constants display the values listed. J J J J J

CH=CH = 14-18 Hz (trans) CH=CH = 7-12 Hz (cis) H-C-H = 1-4 Hz

(geminal)

CH3-CH = 5-7 Hz CH3-C=CH = 0-2 Hz

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Ketones Olefinics

The Ketone linkage weakly deshields the protons of adjacent aliphatic groups but strongly deshields the ortho aromatic protons. The ketones are readily soluble in carbon tetrachloride and deutero-chloroform.

Olefinic Protons The carbonyl group of the ketones weakly deshields the geminal olefinic proton but strongly de-shields the cis and trans hydrogens bonded to the beta carbon atom. Its effect is similar to that of the unsaturated carbon atom of the nitrile (-C≡N) functional group.

3-Buten-2-one

trans (ppm)

cis (ppm)

ca 6.1

ca 6.1

δ

a

(ppm)

5.80

Compound H2C=CH-C(=O)-CH3

Solvent CCI4

Substituted Olefinc Ketones

X-

δ

b

(ppm)

δ

a

(ppm)

X

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Solvent

The Sadtler Handbook of Proton NMR Spectra

CH3-O-

7.50

5.52

CCI4

5.69

CDCI3

5.92

CCI4

6.00

CCI4

6.00

CCI4

6,68

CDCI3

7.05

CDCI3

7.27

CDCI3

7.32

CDCI3

7.95

CDCI3

7.95

CDCI3

7.55

6,47

CH3-

CH3-

6.70

6.70

7.51

7.72

Cl-

N≡C-S-

7.42

7.36

6.86

7.95

Coupling and Coupling Constants

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No unusual couplings nor coupling constants are observed in the NMR spectra of the Ketones. The aliphatic three bond vicinal coupling JHC-CH is 6-8 Hz, the aromatic ortho coupling constant varies from 8-9 Hz, and the olefinic coupling constants display the values listed. J J J J J

CH=CH = 14-18 Hz (trans) CH=CH = 7-12 Hz (cis) H-C-H = 1-4 Hz

(geminal)

CH3-CH = 5-7 Hz CH3-C=CH = 0-2 Hz

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Ketones Aromatics

The Ketone linkage weakly deshields the protons of adjacent aliphatic groups but strongly deshields the ortho aromatic protons. The ketones are readily soluble in carbon tetrachloride and deutero-chloroform.

Aromatic Protons The Ketone functional group is one of the strongly deshielding groups in its effect on the ortho aromatic protons, deshielding them about 0.3 ppm in relation to the meta and para hydrogens. The ortho hydrogens of the phenyl ketones resonate at about 7.8 ppm while the meta and ortho hydrogens overlap to form a complex band in the range from 7.1- 7.5 ppm (CCI4 solution).

Phenyl Ketones

δ

b

(ppm)

δ

a

(ppm)

X

Solvent

7.1-7.5

7.80

CCI4

7.2-7.6

7.92

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

7.2-7.6

7.78

CDCI3

Para Substituted Acetophenones

X-

δ

b

(ppm)

δ

a

(ppm)

Solvent

CH3-

7.09

7.69

CCI4

Br-

7.50

7.73

CCI4

7.17

7.75

CCI4

H2N-

6.62

7.77

CDCI3

R-NH-

6.54

7.80

CDCI3

HO-

6.83

7.80

DMSO-d6

Cl-

8.05

8.05

CDCI3

CH3-S-

7.24

7.81

Polysol

6.71

7.95

CDCI3

CH3-O-

6.98

7.97

CDCI3

F-

7.11

7.99

CDCI3

8.05

8.05

CDCI3

7.64

8.00

CDCI3

8.32

8.19

CDCI3

CH3- CH2 -

O2N-

Para Substituted Benzophenones

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The Sadtler Handbook of Proton NMR Spectra

X-

δ

HOBrCH3-

b

(ppm)

δ

a

(ppm)

Solvent

6.88

7.56

DMSO-d6

7.60

7.60

CDCI3

7.22

7.69

CDCI3

6.65

7.73

CDCI3

7.92

7.92

CDCI3

8.39

7.99

TFA

Coupling and Coupling Constants No unusual couplings nor coupling constants are observed in the NMR spectra of the Ketones. The aliphatic three bond vicinal coupling JHC-CH is 6-8 Hz, the aromatic ortho coupling constant varies from 8-9 Hz, and the olefinic coupling constants display the values listed. J J J J J

CH=CH = 14-18 Hz (trans) CH=CH = 7-12 Hz (cis) H-C-H = 1-4 Hz

(geminal)

CH3-CH = 5-7 Hz CH3-C=CH = 0-2 Hz

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Beta Diketones

The beta Diketones are unusual in that two distinct forms with different chemical shifts exist in solution. Their concentration changes with time, normally the keto form predominates when the sample is first dissolved but upon standing, the keto form increases until it becomes the form at higher concentration. The chemical shifts of aliphatic groups bonded to the diketone fragment are weakly deshielded with the aliphatic groups of the enol form resonating at slightly higher field than those of the keto form. Because the enol hydroxyl group is often quite weak and broadened, it is often difficult to locate its resonance in the offset range beiow 10 ppm.

keto

δ

b

1.98

(ppm)

enol

δ

a

-R

(ppm)

δ

e

(ppm)

δ

d

(ppm)

δ

1.88

3.54

2.20

3.86

2.24

4.03

-R

(ppm)

5.29

3.32

2.17

c

-CH3

CCI4

15.0

1.99

2.08

Solvent

5.38

15.0

2.13

Exchangeable Protons

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-CH3

CCI4

6.00

CCI4

6.12

CDCI3

The Sadtler Handbook of Proton NMR Spectra

The hydroxyl group formed during enolization resonates at lower field than nearly any other type of proton. The range of chemical shifts extends from about 1120 ppm depending upon the structure of the beta diketone and the amount of H2O present in the solution. The high field values are usually observed for solutions containing a relatively large percentage of H2O.

Coupling and Coupling Constants As with the mono-ketones, coupling between groups on opposite sides of the carbonyl carbon is usually not observed. Similarly, coupling across the enolized carbonyl group (-C(OH)=CH) is not observed.

Solubility and Solvent Effects The beta Diketones are readily soluble in carbon tetrachloride and deuterochloroform. Because these solvents are least likely to contain large amounts of water which could exchange with and mask the enol -OH resonance, their use is preferable under normal circumstances.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Aldehydes

The aldehydic functional group produces a characteristic band at very low field arising from the resonance of the proton bonded to the carbonyl group. Coupling between this proton and the adjacent aliphatic groups is usually observed in the HNMR spectra of the aliphatic aldehydes. The aldehydic group weakly deshields aliphatic protons but has a relatively strong deshielding effect on the ortho aromatic protons. The aldehydes oxidize easily and their HNMR spectra often display impurity bands arising from the presence of the corresponding carboxylic acid.

Aliphatic Protons

(ppm)

δ d

(ppm)

δ

(ppm)

δ

c

b

(ppm)

δ a

Compound

Solvent

2.12

CCI

1.09

2.45

CDCI

1.61

2.36

CCI 4

0.95

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4

3

The Sadtler Handbook of Proton NMR Spectra

0.90

1.55

2.43

DMSOd 6

(1.12)

2.38

CCI 4

2.12

2.29

CDCI

1.35

3

(0.98)

Aromatic Protons Benzaldehyde

(ppm)

δ

(ppm)

δ

c

b

9.94

7.79

(ppm)

δ a

7.2-7.6

Solvent

CCI

4

Para Substituted Benzaldehydes

(ppm)

δ

(ppm)

δ

(ppm)

δ

c

b

a

9.66

7.63

6.63

9.78

7.69

6.89

-X

Solvent

CDCI 3

-O-R

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3

CDCI

3

The Sadtler Handbook of Proton NMR Spectra

9.80

7.71

6.92

9.82

7.72

6.92

9.89

7.80

7.04

9.91

7.80

7.19

10.00

7.91

7.21

-F

9.97

7.76

7.31

-CH

9.91

7.73

7.40

-Cl

7.88

7.67

9.97

7.68

7.68

-Br

CDCI

10.13

7.89

8.01

-C≡N

CDCI

8.09

8.39

10.00

-O-R

5

CCI 4 CCI 4

-OH

Acetone CCI 4

CDCI 3

3

CDCI

CDCI

CDCI

3

3

3

3

3

10.18 CDCI

Aldehydic Protons

(ppm)

δ a

-X

Solvent

9.33

CCI 4

9.48

CDCI

3

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3

The Sadtler Handbook of Proton NMR Spectra

9.53

CDCI

9.57

CCI 4

9.58

CCI 4

9.63

CCI 4

9.66

CDCI

9.68

-R

3

CCI 4

9.69

-CH 3

CCI 4

3

9.94

CCI

9.97

CDCI

10.18

CDCI

3

4

3

3

There is a general trend in the chemical shift of the aldehydic proton in relation to the type of group to which it is bonded. In general, the aldehydic protons bonded to vinyl or heteroaromatic groups resonate at slightly higher field than those bonded to aliphatic groups. At the lowest field appear the benzaldehyde protons which are further differentiated in chemical shift by the deshielding effect of other substituents on the aromatic ring as indicated in the table of chemical shifts for para substituted benzaldehydes.

Coupling and Coupling Constants The aldehydic proton normally displays coupling to protons bonded to the carbon atom alpha to the carbonyl group. The coupling constants for such vinyl protons tend to be significantly larger than the corresponding coupling constant observed for aliphatic protons.

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The Sadtler Handbook of Proton NMR Spectra

J J

= =

7.6 Hz 1.4-1.8 Hz

J

=

2.5 Hz

H-C(=O)-CH=C H-C(=O)-CH2-R H-C(=O)-CH(R) 2

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Acid Halides

Due to the limited availability of compounds containing Acid Fluoride, Acid Bromide or Acid Iodide groups, their spectra will deal primarily with the HNMR parameters encountered in the spectra of the Acid Chlorides. The relative deshielding effect of three of the acetyl halides and their hydrolysis product, acetic acid, are presented.

(ppm)

δ

-X

a

Solvent

2.06

-OH

CCI

2.18

-I

CCI 4

2.66

-Cl

CCI 4

2.79

-Br

CDCI

4

Aliphatic Protons

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3

The Sadtler Handbook of Proton NMR Spectra

δ

c

(ppm)

(ppm)

δ b

(ppm)

δ

Compound

a

Solvent

CCI

4

2.66

CDCI 1.22

2.93

1.75

2.88

3

CDCI 0.99

CDCI (1.21)

3

2.59

CCI (1.10)

3

4

2.79

2-Substituted Propionyl Chlorides

(ppm)

δ

(ppm)

δ

b

-X

a

Solvent

2.88

1.75

-CH

2.88

1.77

-C 5

2.62

2.62

CCI

3.02

2.89

CCI 4

3.28

3.28

CDCI 3

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3

CDCI

3

CCI 4

4

The Sadtler Handbook of Proton NMR Spectra

3.51

3.51

-Br

Substituted Acetyl Chlorides

(ppm)

δ a

-X

2.79

2.93

Solvent

CCI

-CH 3

4

CDCI

3

3.80

CCI

4.02

CCI

4.10

CDCI

4.80

CCI

Aromatic Protons Benzoyl Halides

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4

4

3

4

CCI 4

The Sadtler Handbook of Proton NMR Spectra

(ppm)

δ

(ppm)

δ

b

-X

a

Solvent

7.2-7.7

7.94

-F

CCI 4

7.2-7.7

8.02

-Br

CCI 4

7.2-7.7

8.04

-Cl

CCI

4

Para Substituted Benzoyl Chlorides

(ppm)

δ b

(ppm)

δ a

-X

Solvent

7.98

6.89

-O-R

5

CCI 4

8.02

6.90

-O-CH

CCI 4

7.96

7.24

-CH 3

8.02

7.46

-Cl

8.06

7.52

7.94

7.61

-Br

CDCI

8.20

7.73

-CF 3

CDCI

8.22

7.81

-C≡N

CDCI 3

8.21

7.90

CDCI

8.10

8.10

CCI 4

3

CCI

4

CDCI 3 CDCI

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3

3

3

3

The Sadtler Handbook of Proton NMR Spectra

8.26

8.26

CDCI

8.38

8.38

Acetone

3

Solubility and Solvent Effects The Acid Halides are readily soluble in the chlorinated solvents carbon tetrachloride and deuterochloroform. Due to the ease with which the acid halides hydrolyze to form the corresponding carboxylic acid, these solvents are preferable to those such as Polysol, Acetone or DMSO-d6 which may contain traces of water.

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Anhydrides

The anhydrides are similar to other carbonyI containing compounds in that, adjacent aliphatic groups are weakly deshielded while the ortho aromatic protons are strongly deshielded. Their HNMR spectra are similar to those of the carboxylic acids. Be-cause the anhydrides hydrolyze easily to form the corresponding carboxylic acid, the chemical shift range from 10-12 ppm should be checked carefully to determine the presence of the car-boxylic acid -OH group which would indicate that hydrolysis has occurred and to what extent such decomposition products are present in solution.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

(ppm) a 2.20

Compound

Solvent CCI4

1.17

2.43

CCI4

1.69

2.40

CCI4

(1.24)

2.68

CDCI3

1.65

2.48

CDCI3

1.01

0.95 1.45

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The Sadtler Handbook of Proton NMR Spectra

1.60)

2.29

CCI4

(0.97

(1.25)

CCI4

Aromatic Protons Benzoic Anhydride

δ

b

(ppm)

7.2-7.7

δ

a

(ppm)

Compound

8.11

Solvent

CDCl3

Coupling and Coupling Constants The anhydrides display no special couplings nor coupling constants, other than the usual aliphatic H—C—C—H coupling and the normal aromatic ortho and meta couplings that are commonly ob-served for most functional groups.

Solubility and Solvent Effects The anhydrides are readily soluble in carbon tetrachloride and deuterochloroform which are the solvents of preference. Solvents such as DMSOd6, Polysol and Acetone-d6 could contain sufficient amounts of water to lead to the decomposition of the sample.

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Primary Amides

Although similar in chemical shifts to the other carbonyl containing compounds, the Primary Amides can be distinguished by the presence of one or two very broad bands at low field (5.5-8.9 ppm) arising from the resonance of the two -NH2 protons. These bands are exchangeable and will not be observed if D2O or TFA are used as the solvent. Due to the partial double bond character of the amide—C(=O)—NH2 bond, the two NH protons may be non-equivalent resulting in two distinct but overlapping resonance bands.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

(ppm) b 1.98

2.23

δ

a

(ppm)

Compound

Solvent D2O

6.0-7.5

CDCI3

1.12

0.94

2.28

D2O

1.62

2.39

5.6-6.2

CDCI3

(1.19)

(0.98)

2.11

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D2O

The Sadtler Handbook of Proton NMR Spectra

Substituted Acetamides

δ

b

(ppm)

δ

6.0-7.5

a

-X

(ppm)

2.23

Solvent

-CH3

CDCI3

2.28

D2O

7.0, 7.4

3.00

DMSO-d6

5.1-5.7

3.56

CDCI3

7.3, 7.6

3.59

-C≡N

5.5-8.0

3.89

-O-CH3

4.18

-Cl

DMSO-d6 CDCI3 D2O

4.19

TFA

2-Substituted Propionamides

δ

c

(ppm) 6.5-7.1

δ

b

(ppm)

δ

a

(ppm)

-X

2.43

Solvent DMSO-d6

2.43

6.2, 6.9

CCI4

2.59 2.59

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The Sadtler Handbook of Proton NMR Spectra

6.1-6.7

2.61

CDCI3 2.61

6.6-7.3

2.48

DMSO-d6 2.62

TFA

3.00 3.00

5.7-6.7

2.54

CDCI3 3.12

6.6-7.2

2.72

5.9, 6.4

2.74

3.85

-Cl

Acetone-d6 CDCI3

4.38

Aromatic Protons Benzamide

δ

b

(ppm)

δ

7.3-7.9

a

-X

(ppm)

Solvent

8.00

TFA

Para Substituted Benzamides

δ

c

(ppm)

δ

b

(ppm)

δ

a

-X

(ppm)

Solvent

6.5-7.0

7.62

6.60

-NH2

Poly so I

7.1-7.7

7.90

6.94

-O-CH3

Poly so I

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The Sadtler Handbook of Proton NMR Spectra

7.1-7.8

6.8-7.6

7.87

7.61

-Br

DMSOd6

7.92

7.43

-CH3

TFA

7.62

7.78

DMSOd6

Exchangeable Protons The two exchangeable Primary Amide protons resonate at low field as either one or two very broad bands. The table of chemical shifts provided below indicates that the aliphatic Primary Amides resonate at slightly higher field than the aromatic compounds. The chemical shift(s) of these protons vary over a relatively wide range of values due to their sensitivity to the concentration of the sample solution, the solvent employed and the temperature at which the solution was examined, in addition to any possible hydrogen bonding effects and other structural considerations.

δ

a

-X

(ppm)

Solvent

5.5-6.9

-R7

CDCI3

5.8-6.9

-R6

CDCI3 CCI4

5.9, 6.5

6.0-7.5

-R2

CDCI3

6.0-7.0

CDCI3

6.8-7.5

DMSO

7.3-8.3

DMSO

7.6-8.9

DMSO-d6

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Secondary Amides

The HNMR spectra of the Secondary Amides are usually more complex than the primary amides due to the presence of a substituent bonded to the amide nitrogen atom. These substituents produce a much wider range of chemical shifts for the amide proton which may, in addition, display coupling to aliphatic groups bonded to it. The chemical shifts of aliphatic groups bonded to the carbonyl side of this functional group are similar to those observed for the Primary Amides, while those groups bonded to the-nitrogen side of the linkage resonate at slightly lower field than the corres-ponding amines (ca 0.4 ppm).

Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Compound

1.99

D2O

2.27

CDCI3

2.27

1.17

Solvent

2.24

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CDCI3

CDCI3

The Sadtler Handbook of Proton NMR Spectra

2.35

CDCI3

2.29

CDCI3

2.54

Poly so I

1.19

0.92

1.64

(1.12)

CDCI3 (1.20)

Poly so I (1.23)

2.66

CDCI3

2.79

CDCI3

2.80

CDCI3

2.97

CDCI3

3.21

Polysol

3.29

D2O

3.39

CDCI3

3.20

CDCI3

1.10

1.15

1.20

0.90

1.51

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The Sadtler Handbook of Proton NMR Spectra

CDCI3 (1.40)

Olefinic Protons The olefinic protons of the Acrylamides display the same differentiation in chemical shifts noted for the other carbonyl containing groups, i.e. the protons bonded to the beta carbon are deshielded in comparison to the geminal proton which is bonded to the alpha carbon.

δ

b

(ppm)

δ

a

-X

(ppm)

Solvent

5.52

CDCI3

5.9-6.3

Aromatic Protons Both sides of the Secondary Amide linkage deshield the ortho aromatic protons. The protons ortho to the NH group resonate near 7.5 ppm while the protons ortho to the carbonyl group resonate at slightly lower field near 7.8 ppm.

N-Substituted Benzamides

δ

b

(ppm)

δ

a

-X

(ppm)

Solvent

6.8-7.7

7.81

CDCl3

7.2-7.6

7.74

CDCl3

N-Phenyl Amides

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

-X

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Solvent

The Sadtler Handbook of Proton NMR Spectra

7.20

7.05

7.52

CDCl3

7.25

7.12

7.54

CDCl3

Para Substituted Acetanilides

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

-X

Solvent

2.03

7.30

6.71

-OH

Polysol

2.02

7.48

6.85

-O-CH3

DMSO-d6

2.11

7.40

6.99

-F

CDCl3

2.05

7.45

7.03

-CH3

DMSO-d6

2.07

7.32

7.04

2.10

7.68

7.32

2.10

7.40

7.28

2.18

7.60

7.60

-CF3

CDCl3

2.10

7.45

7.61

-Br

DMSO-d6

2.11

7.47

7.61

2.44

7.19

7.70

2.48

7.82

8.35

CDCl3

-Cl

DMSO-d6

CDCl3

Polysol

-I

Coupling and Coupling Constants Clear coupling is normally observed between the NH group and the protons of adjacent hydrocarbon groups. j hn-ch = 4.8-5.2 Hz

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TFA

TFA

The Sadtler Handbook of Proton NMR Spectra

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The Sadtler Handbook of Proton NMR Spectra

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Tertiary Amides

A characteristic feature of the HNMR spectra of the Tertiary Amides is the non-equivalence in chemical shift of similar groups bonded to the nitrogen nucleus. In the case of the N,N-dimethyl amides, the methyl groups range in appearance from a broad single peak to two distinct bands separated by about 10 Hz. The chemical shifts of aliphatic groups bonded to the carbonyl side of the Amide linkage are similar to those observed for the Primary and Secondary Amides.

Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

X

Solvent

2.89

CCI4

(2.94)

CCI4

2.94

D2O

(3.11)

D2O

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The Sadtler Handbook of Proton NMR Spectra

(2.99)

CCI4

(3.23)

CDCI3

3.31

CDCI3

3.37)

CDCI3

3.36

D2O

3.40)

D2O

3.81

CDCI3

3.17

CDCI3

3.21)

CDCI3

3.27

D2O

1.12

(1.20

1.11

(1.11

1.11

0.89

(0.89

0.88

1.58

1.58

1.55

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The Sadtler Handbook of Proton NMR Spectra

(0.91

0.89

3.29)

D2O

3.69

CDCI3

3.69)

CCI4

1.55

1.56

(1.29

The aromatic pattern produced by the Tertiary Amide nitrogen atom depends primarily on whether there are one or two phenyl groups bonded to the nitrogen atom. The aromatic protons of the N-phenyl compounds appear as a complex band over the chemical shift range from 7.-7.6 ppm while those of the N,Ndiphenyl compounds appear as a single peak centered at about 7.3 ppm.

δ

a

(ppm)

Compound

Solvent

ca 7.22

CCI4

ca 7.33

CDCI3

7.0-7.6

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

7.0-7.6

CDCI3

7.1-7.6

CDCI3

Para Substituted Tertiary Benzamides

X-

δ

b

(ppm)

δ

a

(ppm)

-X

Solvent

CH3-O-

7.11

7.53

D2O

Cl-

7.71

7.98

TFA

R-SO2-

7: 87

7.52

CDCI3

R-SO2-

7.87

7.52

CDCI3

CH3-SO2-

7.92

7.52

CDCI3

8.16

7.42

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

8.22

7.50

Polysol

8.29

7.60

CDCI3

Solubility and Solvent Effects The low molecular weight Tertiary Amides are often most soluble in D2O or DMSO-d6 while the higher molecular weight materials are usually more soluble in CCI4 or CDCI3. For the difficulty soluble material, Trifluoroacetic Acid is often effective although its use results in unusually low field chemical shifts for hydrocarbon groups adjacent to both the carbonyl side and the nitrogen side of the Tertiary Amide group.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Imides

The Imides are nitrogen containing analogs of the Anhydrides. They contain the -C(=O)-NH-C(=O)-linkage and are usually cyclic in structure. As with the other carbonyl containing compounds, the protons of aliphatic groups alpha to the C(=O) group are weakly deshielded. The Imide NH proton resonates at low field (812 ppm) and is usually a very broad absorption band.

Aliphatic Protons

δ b (ppm)

1.18

δ a (ppm)

Compound

Solvent

2.30

CDCI3

2.99

CDCI3

3.23

TFA

3.55

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

1.29

3.71

CDCI3

Olefinic Protons The ring olefinic protons of Maleimide appear as a single sharp peak in the chemical shift range from 6.6 to 7.2 ppm. The olefinic protons of a vinyl group bonded to the Imide nitrogen atom are well differentiated in chemical shift. The hydrogen in the geminal position resonates at lowest field (6.83 ppm) as a doublet of doublets due to coupling to the hydrogens cis and trans to it. These hydrogens resonate at higher field, the cis proton at 5.01 ppm as a 10 Hz doublet and the trans proton at 6.02 ppm as a 16 Hz doublet.

Aromatic Protons Phenyl groups bonded to the Imide nitrogen atom usually appear as a single, relatively sharp band near 7.4 ppm. The four aromatic hydrogens of the Phthalimides are observed as a symmetrical, higher-order series of bands centered at about 7.8 ppm.

Exchangeable Protons The chemical shift of the Imide NH proton, as noted above resonates over a range of about 4 ppm at low field. The major determining factor producing this range is the type of ring system in which the Imide group is found. Generally the alicyclic systems, Succinimide and Glutarimide contain NH protons resonating at highest field, the Maleimides occupy the middle of the range, while the Phthalimides appear at the low field end of the range.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Hydrazides

The Hydrazides are similar to the other Amide-like structures in the chemical shifts of protons bonded to carbons alpha to the carbonyl group. The most distinguishing feature of the Hydrazides is the very broad two or three proton band in the range from 3-6 ppm which represents the resonance of the -NH2 exchangeable hydrogens. The NH proton may be in exchange with the NH2 and may resonate in the same range or, if not in exchange, will appear at lower field (7-10 ppm).

Aliphatic Protons

δ c (ppm)

0.90

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent

1.93

CDCl3

1.11

2.21

Polysol

1.58

2.11

DMSO-d6

(2.66)

CDCl3

Aromatic Protons Benzoic Acid, Hydrazides http://www.knowitall.com/handbook/hnmr/hydrazides/hydrazides.html（第 1／3 页）2005-10-2 8:56:17

The Sadtler Handbook of Proton NMR Spectra

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent

7.2-7.6

7.88

DMSO

7.1-7.5

7.82

CDCI3

Para Substituted Benzoic Acid, Hydrazides

δ

b

(ppm)

δ

a

(ppm)

-X

Solvent

7.72

7.23

-CH3

CDCI3

7.88

7.62

-Br

DMSO

8.07

8.22

Polysol

Exchangeable Protons Because the Hydrazides are soluble in solvents which may contain significant amounts of water, it is often difficult to characterize the exchangeable proton resonances with confidence. In gen-eral, it appears that the NH2 group resonates at intermediate field and is often in exchange with any water which may be present in the solution producing an erroneous 3-hydrogen integration value. In addition, the C(=O)-NH proton may resonate at much lower field (7-9 ppm) as a very broad band which may be difficult to locate.

δ

b

(ppm) 4.5

δ

a

(ppm)

Compound

7.7

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Solvent DMSOd6

The Sadtler Handbook of Proton NMR Spectra

3.9

8.0

Polysol

4.5

9.1

DMSOd6

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Ureas

The monosubstituted aliphatic ureas characteristically display separate resonance bands for the two different types of NH protons. Coupling is usually observed between the NH and the protons of the adjacent hydrocarbon group (NH-CH2). The chemical shift of aliphatic groups adjacent to the Urea nitrogen nucleus varies with the degree of substitution of the urea moiety as well as the other types of substituents in the molecule.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

X

Solvent D2O

(1.29)

3.99

2.70

CCI4 (2.75)

CDCI3

2.78

CDCI3 (2.91)

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The Sadtler Handbook of Proton NMR Spectra

CDCI3

(2.97)

CDCI3

3.16

CDCI3 1.11

3.18

CDCI3 1.22

3.50

Polysol (1.09)

3.72

0.96

CDCI3 1.35

1.50

3.15 Polysol

(1.29)

Polysol (0.90)

1.69

2.91

Aromatic Protons The 1-phenyl ureas display an unusual type of aromatic shielding, i.e. the para proton is shielded while the ortho protons are deshielded. This shielding is not observed when two phenyl groups are bonded to the same nitrogen atom. In this case, a single peak is often observed near 7.3 ppm.

Phenyl Substituted Ureas

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

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-X

Solvent

The Sadtler Handbook of Proton NMR Spectra

7.02

7.32

DMSO

7.58

6.8-7.5

CDCI3

ca 7.25

CDCI3

ca 7.27

Polysol

Exchangeable Protons Substitution of a urea molecule deshields the adjacent NH proton in comparison to the unsubstituted NH2 group in the same molecule.

δ

b

(ppm)

δ

a

(ppm)

-X

Solvent

5.21

5.63

DMSOd6

5.21

5.74

Polysol

5.39

5.92

Polysol

5.22

6.00

Polysol

5.29

6.35

Polysol

6.79

6.79

-H

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Polysol

The Sadtler Handbook of Proton NMR Spectra

5.53

8.19

Polysol

5.79

8.39

DMSOd6

5.88

8.62

DMSOd6

Coupling and Coupling Constants Coupling is usually observed between the NH proton and the hydrogens of adjacent hydrocarbon groups. The coupling constant varies over the range from 68. It is interesting to note that the type of non-equivalence so common in the spectra of N,N-dimethylamides is not observed in the HNMR spectra of the N,Ndimethylureas.

Solubility and Solvent Effects The solubility of the ureas varies primarily with the degree of substitution and the type of substituent(s). Urea and its monosubstituted derivatives are generally more soluble in solvents such as D2O, DMSO-d6 and Polysol. The trisubstituted and tetrasubstituted compounds, as well as those with large hydrocarbon groups tend to be more soluble in carbon tetrachloride or deuterochloroform. There does not appear to be any unusual solvent effects when CCl4, CDCI3, DMSO-d6 and Polysol are used. As with most compounds, D2O exchanges with the labile hydrogens in the molecule resulting in the loss of their resonance bands, and the use of trifluoroacetic acid produces unusually low field chemical shifts.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Hydantoins and Uracils

The Hydantoins and Uracils are cyclic structures containing the group – NH-C(=O-NH-C(=O)-. Hydantoin is a five membered ring while Uracil is a six membered ring. When present, the NH proton at position one (adjacent to one carbonyl) resonates at higher field than the NH proton at position three (adjacent to two carbonyl groups). Aliphatic groups bonded to the rings possess chemical shifts determined by their position on the ring.

Hydantoins

δ

b

(ppm)

δ a(ppm)

Group

Ring System

Solvent Polysol

1.31

CH3-

CDCI3 (1.38)

(CH3)2-

DMSO-d6 1.68

CH3-

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The Sadtler Handbook of Proton NMR Spectra

CDCI3

3.00

CH3-

CDCI3

1.12

3.47

CH3-CH2-

Cyclic Protons

δ

c

(ppm)

7.44

δ

b

(ppm)

9.52

δ

a

-X

(ppm)

Solvent

4.03

-CH3

Polysol

4.29

-H

TFA DMSO-d6

8.34 10,74

5.14

7.92

5.39

6.94

DMSO-d6

Uracils Aliphatic Protons

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The Sadtler Handbook of Proton NMR Spectra

δ

a

Group

(ppm)

Ring System

Solvent DMSO-d6

1.75

CH3

TFA 2.05

CH3

TFA 2.38

CH3

CDCI3

3.30

CH3

CDCI3

3.41

CH3

Cyclic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Solvent

-CH3

7.21

DMSO

-CH3

-CH3

5.71

7.29

CDCI3

10.55

10.56

-Br

7.71

DMSO

9.10

9.10

-I

7.88

DMSO

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The Sadtler Handbook of Proton NMR Spectra

11.69

8.80

DMSO

11.69

10.10

-CH3

-CH3

TFA

10.19

6.02

-CH3

TFA

Solubility and Solvent Effects The cyclic diamides such as Hydantoin and Uracil are normally not soluble in carbon tetrachloride nor deuterochloroform unless one or both of the nitrogen atoms are substituted by an aliphatic group. The compounds are usually readily soluble in Polysol, DMSO-d6, acetone and trifluoroacetic acid. Trifluoroacetic acid is usually the solvent of last choice since one or both of the NH resonance bands may not be observed due to overlap with the acid proton band at low field.

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Carboxylic Acids Aliphatics

The carboxylic acid functional group (-C(=O)-OH) has a weakly deshielding effect on the protons of adjacent aliphatic groups but a strongly deshielding effect on the ortho aromatic protons. A distinguishing feature of this group of compounds is the carboxylic acid -OH group which normally resonates at very low field (10-13 ppm). This band may appear at higher field when a significant amount of water is present in the solution.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm) 2.06

(ppm) a 11.90

2.37

10.49

CDCI3

2.29

11.97

CCI4

2.55

12.08

CCI4

δ

Compound

Solvent CCI4

1.14 0.90 1.67

(1.20)

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The Sadtler Handbook of Proton NMR Spectra

(0.98)

2.19

11.00

CCI4

12.01

CDCI3

12.08

CCI4

2.08

(1.21)

(0.93

2.21 1.55)

Substituted Acetic Acids

δ

b

(ppm)

δ

a

(ppm)

10.49

2.37

11.80

2.43

10.08

3.12

-X

Solvent

-CH3

CDCI3 DMSO-d6

-CH=CH2

CDCI3

11.28

3.25

CDCI3

11.50

3.37

Polysol

3.61

CDCI3

10.88

10.80

3.71

-I

CDCI3

11.49

3.79

11.75

3.79

-C≡N

DMSO-d6

10.59

3.92

-Br

CDCI3

11.22

4.05

-Cl

CCI4

4.10

-O-CH3

D2O

4.29

-OH

D2O

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

8.78

4.67

Acetone

Alicyclic Protons

n 2

δ

(ppm) δ (ppm) δ (ppm) c b a (0.71.58 11.72 1.2)

Solvent CCI4

3

(1.62.7)

3..19

11.99

CDCI3

4

(1.22.2)

2.69

11.25

CCI4

5

(1.1-26)

2.25

12.00

CCI4

6

(1.12.2)

2.53

11.55

CDCI3

Exchangeable Protons The carboxylic acid protons which are extremely labile hydrogens exchange with many other types of labile hydrogen to produce an averaged chemical shift for the protons involved in the exchange. In addition, they will be in exchange with any water present in the solution resulting in either higher-field chemical shifts than expected and/or very broad resonance bands covering several ppm. The latter case is much more noticeable in the HNMR spectra of the Benzoic acids than in the spectra of the more soluble aliphatic compounds.

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Carboxylic Acids Olefinics

The carboxylic acid functional group (-C(=O)-OH) has a weakly deshielding effect on the protons of adjacent aliphatic groups but a strongly deshielding effect on the ortho aromatic protons. A distinguishing feature of this group of compounds is the carboxylic acid -OH group which normally resonates at very low field (10-13 ppm). This band may appear at higher field when a significant amount of water is present in the solution.

Olefinic Protons The three olefinic protons of acrylic acid resonate as a complex higher-order pattern in the chemical shift range from 5.7-6.8 ppm. The most deshielded of these protons is the hydrogen that is cis to the carboxylic acid group, while the geminal proton resonates at higher field. This order of chemical shifts is the reverse of that observed for simple alkenes.

3-Substituted acrylic acids

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

12.28

6.66

6.66

12.27

6.27

6.84

11.91

5.77

7.03

11.79

5.82

11.34 11.90

-X

Solvent (trans)

DMSOd6

-Cl

(cis)

Polysol

-R3

(trans)

CCI4

7.04

-CH3

(trans)

CDCI3

6.28

7.50

-Cl

(trans)

CDCI3

6.41

7.73

(trans)

CDCI3

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11.00

6.90

7.75

(trans)

CDCI3

Exchangeable Protons The carboxylic acid protons which are extremely labile hydrogens exchange with many other types of labile hydrogen to produce an averaged chemical shift for the protons involved in the exchange. In addition, they will be in exchange with any water present in the solution resulting in either higher-field chemical shifts than expected and/or very broad resonance bands covering several ppm. The latter case is much more noticeable in the HNMR spectra of the Benzoic acids than in the spectra of the more soluble aliphatic compounds.

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Carboxylic Acids Aromatics

The carboxylic acid functional group (-C(=O)-OH) has a weakly deshielding effect on the protons of adjacent aliphatic groups but a strongly deshielding effect on the ortho aromatic protons. A distinguishing feature of this group of compounds is the carboxylic acid -OH group which normally resonates at very low field (10-13 ppm). This band may appear at higher field when a significant amount of water is present in the solution.

Aromatic Protons Benzoic Acid

δ

c

(ppm)

δ

7.2-7.8

b

(ppm)

8.14

δ

a

(ppm)

12.82

Solvent CCI4

Para Substituted Benzoic Acids

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

-para

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Solvent

The Sadtler Handbook of Proton NMR Spectra

6.55

7.83

6.76

-NH2

Acetone

10.95

7.95

6.90

-O-R3

Polysol

7.91

7.00

-O-CH3

DMSO-d6

9.76

8.11

7.07

-OH

Acetone

12.02

8.09

7.20

9.72

8.02

7.30

-F

Acetone

8.02

7.30

-CH3

TFA

8.27

8.00

7.56

-Cl

DMSO

7.28

7.90

7.71

-Br

DMSOd6

7.90

7.71

-I

DMSO-d6

8.11

8.11

DMSOd6

8.21

8.30

DMSOd6

9.41

DMSO

Exchangeable Protons The carboxylic acid protons which are extremely labile hydrogens exchange with many other types of labile hydrogen to produce an averaged chemical shift for the protons involved in the exchange. In addition, they will be in exchange with any water present in the solution resulting in either higher-field chemical shifts than expected and/or very broad resonance bands covering several ppm. The latter case is much more noticeable in the HNMR spectra of the Benzoic acids than in the spectra of the more soluble aliphatic compounds.

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Carboxylic Acids Amino Acids

The Amino Acids, and especially the alpha amino acid's, are distinguished by their high degree of solubility in water (D2O) and that many of these compounds contain a methine resonance band at relatively low field (3.3-4.5 ppm). Because the methine proton of the alpha Amino Acids is an asymmetric carbon, an adjacent methylene group may display clear non-equivalence in chemical shift for the two hydrogens bonded to it. As a result, the methine proton may appear as a doublet of doublets rather than as a triplet.

Aliphatic Protons

δ

a

-N (X,Y)

(ppm)

3.58

-NH 2

3.62

-NH-CH

3.68

Solvent D2O

3

D2O D2O

3.81 D2O

3.81 D2O

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The Sadtler Handbook of Proton NMR Spectra

3.90 D2O

3.92 D2O

3.98

δ

a

D2O

-X

(ppm)

3.30

Solvent D2O

3.50 D2O

3.55 D2O

3.70

-CH

3.70

- CH2 - CH

3.71

-R

D2O

3

3

3

D2O D2O

3.79 D2O

3.82

D2O

3.91

D2O

4.00 D2O

4.47

-CH2-SH

D2O

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Salts of Carboxylic Acids

The Salts of the Carboxylic Acids are very similar in most respects to their corresponding Carboxylic acids with the exception of their increased solubility in water (D2O). The chemical shifts listed vary over a relatively wide range due to the different solvents employed. The solubility of the Carboxylic Acid Salts, in turn, is directly related to the metal which is present in the compound.

Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

X

Solvent

1.88

D2O

1.90

DMSO-d6

1.90

CDCI3

1.99

D2O

D2O 1.01

2.30) (1.09

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D2O

The Sadtler Handbook of Proton NMR Spectra

2.17 0.90

D2O

1.56

Substituted Acetic Acid Salts

Group

δ

a

X

(ppm)

Solvent

Na-O-C(=O)-

3.11

D2O

Na-O-C(=O)-

3.19

D2O

-Sn-O-C(=O)-

3.50

CCI4

Na-O-C(=O)-

3.51

K-O-C(=O)-

3.53

D2O

-Hg-O-C(=O)-

3.60

Poly so I

Na-O-C(=O)-

3.63

Na-O-C(=O)-

4.25

Na-O-C(=O)-

4.73

-SH

D2O

-l

D2O D2O

-F

D2O

Olefinic Protons The vinyl protons of Acrylic Acid salts appear as a higher-order series of peaks in the chemical shift range from 5.5-6.3 ppm. Characteristically, the two protons on the beta carbon are more strongly deshielded than the proton on the alpha carbon atom.

2-Substituted Acrylic Acid Salts

δ

b

(ppm) δ

a

(ppm)

-X

Solvent

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The Sadtler Handbook of Proton NMR Spectra

6.02

6.02

(cis)

D2O

6.10

6.10

(cis)

D2O

6.50

6.50

(trans) D2O

5.84

6.59

-CH3

D2O

5.75

6.75

-CH3

(trans) CCI4

6.76

6.76

(trans) CDCI3

6.53

7.54

(trans) D2O

Aromatic Protons Salts of Benzoic Acid

δ

b

(ppm) 7.3-7.7

δ

(ppm) a 7.91

Compound

Solvent D2O

7.3-7.6

7.98

D2O

7.3-7.7

7.99

D2O

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The Sadtler Handbook of Proton NMR Spectra

7.2-7.7

8.05

Poly so I

Aldehydic Protons Salts of Formic Acid

δ

a

(ppm)

-X

8.08

Solvent CCI4

8.17

-Na

TFA

8.46

-Li

D2O

8.48

-Ca-

D2O

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Aliphatic Esters

The Esters are one of the most important functional groups with a wide variety of combinations of aliphatic, olefinic and aromatic acids and alcohols. The carbonyl side of the ester functional group has a weakly deshielding effect on the protons of adjacent aliphatic groups, while the oxygen side of the linkage has a strongly deshielding effect. The Esters are readily soluble in carbon tetrachloride and deuterochloroform unless substituted by more polar functional groups.

Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent

1.90

CCI4

1.95

CCI4

2.00

CCI4

1.10

2.27

CCI4

1.10

2.27

CCI4

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The Sadtler Handbook of Proton NMR Spectra

1.16

2.30

CDCI3

0.95

1.70

2.18

CCI4

0.91

1.61

2.21

CCI4

(1.13)

2.44

CCI4

(1.14)

2.49

CCI4

CCI4

(1.17)

(0.96)

1.97

2.12

CCI4

(0.93)

1.99

2.18

CDCI3

3.61

CCI4

3.65

CCI4

3.70

CCI4

4.00

CCI4

1.23

4.07

CCI4

1.29

4.19

CCI4

1.41

4.41

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

0.98

1.67

4.08

CCI4

0.98

1.78

4.30

CDCI3

(1.22)

4.92

CCI4

(1.39)

5.20

CCI4

1.97

3.89

CCI4

(0.96)

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Olefinic Esters

The Esters are one of the most important functional groups with a wide variety of combinations of aliphatic, olefinic and aromatic acids and alcohols. The carbonyl side of the ester functional group has a weakly deshielding effect on the protons of adjacent aliphatic groups, while the oxygen side of the linkage has a strongly deshielding effect. The Esters are readily soluble in carbon tetrachloride and deuterochloroform unless substituted by more polar functional groups.

Olefinic Protons The olefinic protons of Acrylic Acid Esters appear in the HNMR spectrum as a higher-order ABC pattern in the chemical shift range from 5.6-6.1 ppm. The proton which is trans to the carbonyl group resonates at highest field, the geminal proton resides at slightly lower field, and the hydrogen which is cis to the carbonyl appears at lowest field.

Acrylate Esters

δ

c

(ppm)

6.34

δ

b

(ppm) 5.72

δ

a

(ppm) 6.09

Compound

Solvent CCI4

The Vinyl Esters of aliphatic carboxylic acids produce a much clearer pattern than the corresponding Acrylic Acid protons. The three olefinic protons of the Vinyl Esters produce resonance bands over the range from 4.3 to 7.5 ppm. The two protons bonded to the beta carbon resonate at highest field while the geminal proton which is bonded to the alpha carbon resonates at lower field.

Vinyl Esters of Aliphatic Acids

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The Sadtler Handbook of Proton NMR Spectra

δ

c

(ppm)

δ

(ppm)

b

4.82

δ

4.51

a

X

(ppm)

Solvent

7.23

CDCI3

2-Substituted Acrylate Esters

R-

δ

(ppm) b 6.79

δ

a

(ppm)

-X

6.79

-R7

Solvent (trans)

CCI4

(trans)

CCI4

(trans)

CDCI3

(trans)

CCI4

5.71

6.84

6.86

6.86

5.79

6.90

6.59

7.03

(trans)

CDCI3

6.40

7.67

(trans)

CCI4

-CH3

The Aldehydic Protons The Aldehydic protons of the Formic Acid esters appears as a sharp singlet at low field in the range from 7.9 to 8.10 ppm.

δ

a

-X

(ppm)

7.90

Solvent CCI4

7.91

-R7

CCI4

7.96

-R

8

CCI4

7.98

-CH3

CCI4

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The Sadtler Handbook of Proton NMR Spectra

8.07

CDCI3

8.10

CDCI3

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Aromatic Esters

The aliphatic esters of Benzoic Acid are more highly deshielded by the adjacent oxygen atom than those of the aliphatic and olefinic carboxylic acids. The ortho aromatic protons are also strongly deshielded by the adjacent carbonyl group and resonate about 0.5 ppm to lower field than the meta and para protons. The aromatic esters are readily soluble in the halogenated solvents normally used as solvents in NMR and do not exhibit any unusual solvent effects. These compounds do not display any special spin-spin couplings.

Aromatic Protons The carbonyl side of the ester linkage strongly deshields the ortho aromatic protons producing a series of multiplets similar to those observed for the ketones and amides. The oxygen side of the group has a much weaker shielding effect than the oxygen atom of the aliphatic ethers, resulting in a broad, complex higher-order series of multiplets in the chemical shift range from 6.9-7.5 ppm.

Benzoic Acid, Propyl Ester

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent

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The Sadtler Handbook of Proton NMR Spectra

7.1-7.6

8.01

CCI4

Propionic Acid, Phenyl Ester

δ

a

Compound

(ppm)

Solvent

6.9-7.5

CCI4

Para Substituted Phenyl Esters

δ

(ppm)

-X

6.82

7.01

-CH3

CCI4

7.06

7.06

-F

CDCI3

7.09

7.09

CDCI3

7.19

7.80

CCI4

7.19

7.88

CDCI3

7.32

8.29

CDCI3

b

(ppm)

δ

a

Solvent

Para Substituted Benzoic Acid Esters

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The Sadtler Handbook of Proton NMR Spectra

δ

(ppm)

-X

7.83

6.63

-NH2

CDCI3

7.87

6.84

-OH

CDCI3

7.99

6.88

-O-CH3

CDCI3

7.95

7.06

-N=C=O

CDCI3

7.88

7.36

7.95

7.38

-Cl

CDCI3

7.83

7.49

-Br

CCI4

7.82

7.70

-I

8.32

7.91

-N=O

8.07

8.07

CDCI3

8.26

8.26

CDCI3

b

(ppm)

δ

a

Solvent

CCI4

Polyso I CDCI3

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Lactones

Due to their cyclic structure, the aliphatic cyclic esters often display non-equivalence in chemical shift for the two protons of the methylene group in the ring system. This situation is clearly observed in compounds in which the five ring hydrogens each display distinctly different chemical shifts. The aromatic protons of the aromatic lactones generally pro-duce complex patterns in the chemical shift range from 6.5 to 8.0 ppm depending upon which group of the ester moiety is bonded to the aromatic ring. When the oxygen atom is bonded to the ring, the resonance bands tend to be in the high field portion of the range, 6.8 -7.4. When the carbonyl group is bonded to the aromatic ring, then the resonance bands tend to occupy the lower half of the range. The Lactones, like the other esters are readily soluble in the chlorinated NMR solvents, carbon tetrachloride and deuterochloroform.

Alicyclic Protons

δ

c

(ppm)

δ b (ppm)

δ

a

(ppm)

Compound

Solvent

4.40

1.5-2.1

2.1-2.7

CCI4

3.9-4.4

1.9, 2.4

2.60

CCI4

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4.2, 4.6

3.69

2.6, 2.8

CDCI3

4.3, 4.6

2.2-2.8

3.00

CCI4

4.29

1.9-3.0

3.71

CCI4

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Chloroformates

The aliphatic esters of Chloroformic Acid are notable in that their alpha hydrocarbon groups are more strongly deshielded than either the esters of simple aliphatic or aromatic carboxylic acids. The Chloroformates are readily soluble in the chlorinated solvents. Their spectra display no unusual couplings nor coupling constants.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

1.40

1.00

1.76

1.75

1.45

(0.99)

2.08

1.01

δ

a

(ppm)

X

Solvent

3.93

CCI4

4.39

CDCI3

4.22

CCI4

4.31

CCI4

4.11

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

δ

a

Compound

(ppm)

Solvent

CCI4

7.0-7.6

Para Substituted Phenyl Chloroformates

δ

b

(ppm)

δ

a

(ppm)

-X

Solvent

7.03

6.77

-O-CH3

CCI4

7.10

7.30

-Cl

CCI4

7.33

CCI4

8.12

DMSO-d6

7.07

7.11

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Carbamates

The NMR spectra of the Carbamates are often quite complex in appearance since up to three aliphatic or aromatic groups may be present in the molecule. In addition, the secondary Carbamates (R-NH-C(=O)-O-) often display coupling between the NH proton and the hydrogens bonded to the adjacent carbon atom. The coupling constant for this interaction is about 7.5 Hz. Hydrocarbon groups adjacent to the nitrogen side of the linkage are deshielded to intermediate field (about 3 ppm) while those adjacent to the oxygen side are deshielded by an additional 1 ppm to about 4 ppm.

Aliphatic Protons

δ

d

(ppm)

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

(3.06)

Solvent CDCI3

2.78

5.09

CDCI3

3.15

5.57

CCI4

3.08

5.25

CCI4

1.12

0.90

X

1.45

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The Sadtler Handbook of Proton NMR Spectra

3.71

4.66

CDCI3

(1.15)

δ

d

(ppm)

δ

c

(ppm)

1.20

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent

3.60

5.30

CCI4

3.63

5.13

CDCI3

4.03

5.25

CCI4

CCI4

4.07 1.21

4.08

5.20

CDCI3

4.11

5.09

CDCI3

4.10

6.90

CDCI3

4.89

4.97

CDCI3

4.88

CDCI3

1.22

1.24

0.94 1.68

(1.22)

(1.45)

Aromatic Protons Phenyl Carbamates

δ

b

(ppm)

δ

a

(ppm)

Compound

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Solvent

The Sadtler Handbook of Proton NMR Spectra

6.8-7.4

δ

a

(ppm)

6.6-7.5

7.51

DMSO

Compound

Solvent

CDCI3

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Esters of the Phosphorus Acids

The chemical shifts of the Esters of Phosphonic and Phosphoric Acid are similar to those of the carboxylic acids, however, their spectra are distinguished by the spin-spin coupling interactions of the nearby hydrocarbon groups with the Phosphorus nucleus. As noted, many of these couplings and their associated coupling constants are quite sensitive to structural and substituent differences. Both groups of compounds are quite soluble in carbon tetrachloride and deuterochloroform and no unusual solvent effects have been noted for these two solvents.

The Phosphonates Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent

(3.71)

CCI4

(3.72)

CCI4

(3.80)

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

4.01)

CDCI3

4.04)

CCI4

4.08)

CCI4

4.11)

CDCI3

4.11)

CDCI3

4.17)

CCI4

4.22)

CDCI3

3.51)

CCI4

4.64)

CCI4

1.33

CCI4

1.91

CDCI3

(1.22

(1.29

(1.36

(1.31

(1.36

(1.35

(1.40

(0.99

1.65

(1.32

1.19

Substituted Methyl Phosphonates

δ

a

(ppm)

1.91

X

J P(=O)-CH2 (Hz)

Solvent

-CH3

0

CDCI3

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The Sadtler Handbook of Proton NMR Spectra

2.98

-C≡N

20.9

CDCI3

21.3

CDCI3

23.1

CDCI3

3.05

3.10

3.51

-Cl

11.5

CCI4

3.69

-O-CH3

8.0

CCI4

R

J P(=O)-H (Hz)

Solvent

Phosphonyl Protons

δ

a

(ppm)

4.40

-CH3

411 Hz

CCI4

5.69

-C≡N

342 Hz

CCI4

697 Hz

CCI4

733 Hz

CDCI3

691 Hz

CDCI3

5.80

6.11

6.76

-Cl

Aromatic Protons The aromatic protons of the phenyl esters of Phosphonic Acid resonate as a broad, single peak or a complex series of bands centered at about 7.2 ppm. Phenyl groups bonded to the Phosphorus nucleus display a strong deshielding of the ortho protons which resonate near 7.8 ppm and couple to the Phosphorus nucleus with a coupling constant of about 13 Hz.

Phenyl Phosphonates

δ

b

(ppm)

δ

a

(ppm)

Compound

Solvent

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The Sadtler Handbook of Proton NMR Spectra

7.3-7.6

δ

a

7.80

Acetone

Compound

(ppm)

Solvent

ca. 7.21

CDCI3

7.3-7.6

CDCI3

Coupling and Coupling Constants JP

(=O)-C-O-CH = 1.1 Hz 3

JP( =O)-O-CH2 = 7.3-8.1 Hz JP( JP(

=O)-O-CH3 = 10.8 Hz =O)-CH2 = 11-24 Hz

JP( =O)-CH3 = 17.5 Hz JP( =O)-H = 340-740 Hz

Aliphatic Protons

δ

c

(ppm)

δ

b

(ppm)

(1.33

δ

a

(ppm)

Compound

Solvent

(3.75)

CCl4

4.06)

CCl4

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The Sadtler Handbook of Proton NMR Spectra

(1.31

4.11)

CCl4

(0.99

1.70

3.99)

CDCl3

(0.92

1.62

4.00)

CCl4

Aromatic Protons

δ

a

(ppm)

Compound

Solvent

ca 7.20

CDCl3

ca 7.21

CCl4

6.8-7.4

Polysol

Exchangeable Protons

δ

a

(ppm)

8.83

Compound

Solvent

CDCl3

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The Sadtler Handbook of Proton NMR Spectra

(10.19)

Polysol

11.06

CCl4

12.22

CDCl3

Coupling and Coupling Constants J P(=O)-O-CH3 = 10-12 Hz J P(=O)-O-CH2 = 6-7 Hz

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Saturated Hydrocarbons Normal Alkanes

This section contains the carbon-13 NMR chemical shifts of the straight chain alkanes. The aliphatic additivity constants presented in many of the section heading discussions are usually very useful when utilized with these parent alkane chemical shifts in the calculation of theoretical chemical shifts for straight aliphatic compounds.

Alkanes

C-7

C-6

C-5

C-4

C-3

C-2

C-1

Compound

14.2

22.8

34.8

22.8

14.2

CDCl3

14.2

23.0

32.1

32.1

23.0

14.2

CDCl3

14.1

23.1

32.4

29.5

32.4

23.1

14.1

CDCl3

R2-

32.3

29.8

29.8

32.3

23.1

14.1

CDCl3

R5-

30.1

30.1

29.7

32.3

23.0

14.2

CDCl3

R12-

29.9

29.9

29.6

32.2

22.9

14.2

CDCl3

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Solvent

The Sadtler Handbook of Carbon NMR Spectra

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Saturated Hydrocarbons Branched Alkanes

This section contains the carbon-13 NMR chemical shifts of the branched alkanes. The aliphatic additivity constants presented in many of the section heading discussions are usually very useful when utilized with these parent alkane chemical shifts in the calculation of theoretical chemical shifts for branched aliphatic compounds.

2-Methyl Alkanes

C-7

C-6

C-5

C-4

C-3

C-2

C-1

Solvent

11.8

32.0

30.1

22.3

CDCl3

14.1

23.2

29.9

39.0

28.2

22.7

CDCl3

14.2

23.0

32.5

27.3

39.3

28.3

22.8

CDCl3

R2-

32.3

29.9

27.7

39.4

28.3

22..8

CDCl3

3-Ethyl Alkanes

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The Sadtler Handbook of Carbon NMR Spectra

C-7

14.2

C-6

23.4

C-5

C-4

C-3

C-2

C-1

Solvent

18.9

36.6

29.5

11.6

CDCl3

11.1

25.5

42.5

25.5

11.1

CDCl3

29.3

32.8

40.7

25.7

11.0

CDCl3

C-4

C-3

C-2

C-1

Solvent

8.9

36.7

30.5

29.0

CDCl3

2,2-Dimethyl Alkanes

C-7

C-6

C-5

14.1

22.9

33.1

24.4

44.5

30.4

29.5

CDCl3

R2-

32.3

30.6

24.8

44.6

30.4

29.6

CDCl3

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

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Saturated Hydrocarbons Cyclic Alkanes

This section contains the carbon-13 NMR chemical shifts of cyclic hydrocarbons. The chemical shift tables presented below illustrate the carbon resonances of both the ring carbons of substituted forms and the shifts of the side chain carbons of alkyl cycloalkanes.

Cyclopropanes

C-2,3

C-1

-X

Solvent

7.1

-3.5

-C≡N

CDCl3

4.7

11.9

CDCl3

9.1

15.5

CDCl3

Cyclobutanes

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The Sadtler Handbook of Carbon NMR Spectra

C-3

C-2,4

C-1

-X

18.7

25.5

38.5

15.6

27.8

46.2

-NH2 HCl

12.1

33.41

67.0

-OH

Solvent CDCl3

D2O CDCl3

Cyclopentanes

C-3,4

C-2,5

C-1

-X

Solvent

23.9

39.8

28.1

-I

CDCl3

25.6

35.1

35.1

-CH3

CDCl3

25.5

33.1

40.6

-R5

CDCl3

23.4

38.0

53.0

-Br

CDCl3

23.2

37.3

61.8

-Cl

CDCl3

Cyclohexanes

C-4

C-3,5

C-2,6

C-1

-X

Solvent

25.4

24.2

29.7

28.1

-C≡N

CDCl3

26.0

24.9

32.6

28.9

-C≡C-H

CDCl3

25.2

27.1

39.5

32.0

-I

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

26.7

26.7

35.8

33.1

-CH3

CDCl3

27.0

26.7

34.0

35.6

27.1

26.7

33.7

37.9

-R7

CDCl3

25.5

26.3

38.0

38.3

-SH

CDCl3

27.1

26.8

33.3

39.9

-CH2CH3

CDCl3

24.8

24.2

30.4

50.1

-NH2 HCl

Polysol

26.0

25.3

37.1

50.5

-NH2

CDCl3

26.0

25.1

33.4

51.5

25.3

25.9

37.6

52.9

-Br

CDCl3

26.6

29.2

34.0

56.9

-NH-CH2CH3

CDCl3

25.1

24.0

27.6

59.5

-NH-NH2 HCl

Polysol

25.8

24.0

32.0

72.2

CDCl3

25.2

24.4

31.3

84.8

CDCl3

CDCl3

CDCl3

Alkyl Cyclopentanes; Alkyl Shifts

C-5

14.2

C-4

C-3

C-2

C-1

-X

Solvent

20.9

-C5

CDCl3

14.2

23.3

31.5

36.4

-C5

CDCl3

23.0

32.6

28.9

36.6

-C5

CDCl3

Alkyl Cyclohexanes; Alkyl Shifts

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The Sadtler Handbook of Carbon NMR Spectra

C-7

14.1

C-6

C-5

C-4

C-3

C-2

C-1

-X

Solvent

22.9

-C6

CDCl3

11.4

30.4

-C6

CDCl3

14.4

20.1

40.2

-C6

CDCl3

14.2

23.3

29.4

37.6

-C6

CDCl3

14.2

23.0

32.6

26.8

37.8

-C6

CDCl3

14.1

22.9

32.3

30.0

27.1

38.0

-C6

CDCl3

22.9

32.2

29.6

30.2

27.1

37.9

-C6

CDCl3

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Unsaturated Hydrocarbons Acyclic Alkenes

The carbon-13 NMR chemical shifts of alkenes that are contained in this section illustrate the low field chemical shifts of the alkenyl carbon atoms (100150ppm) and the weakly deshielding effect of alkene linkages on the chemical shifts of adjacent aliphatic groups. The aliphatic additivity constants for two forms are given below.

C-4

C-3

C-2

C-1

-X

0.4

-2.5

6.5

19.9

CH2=CH-

0.4

-2.4

5.1

24.0

The Alkenes; Alkyl Chemical Shifts

C-6

C-5

14.1

C-4

C-3

C-2

C-1

-X

Solvent

14.0

22.5

31.6

33.8

-CH=CH2

CDCl3

22.8

31.7

29.0

34.1

-CH=CH2

CDCl3

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The Sadtler Handbook of Proton NMR Spectra

14.1

22.9

32.1

29.1

29.3

34.1

-CH=CH2

CDCl3

R2-

32.2

29.4

29.4

29.4

34.1

-CH=CH2

CDCl3

R7-

29.9

29.9

29.6

29.3

34.0

-CH=CH2

CDCl3

The CIS Alkenes; Alkyl Chemical Shifts

C-5

14.2

C-4

C-3

22.9

C-2

C-1

-X

Solvent

12.7

-CH=CH-R5

CDCl3

12.7

-CH=CH-R3

CDCl3

13.7

23.1

29.2

-CH=CH-CH3

CDCl3

31.9

29.7

27.1

-CH=CH-CH3

CDCl3

The TRANS Alkenes; Alkyl Chemical Shifts

C-5

14.2

C-4

C-3

C-2

C-1

-X

Solvent

17.8

-CH=CH-R3

CDCl3

14.0

17.9

-CH=CH-R5

CDCl3

13.7

23.1

35.0

-CH=CH-CH3

CDCl3

14.1

22.5

32.2

32.6

-CH=CH-R4

CDCl3

22.9

31.9

29.7

33.0

-CH=CH-CH3

CDCl3

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The Sadtler Handbook of Proton NMR Spectra

2,2-Disubstituted Ethenes; Alkyl Chemical Shifts

C-5

C-4

C-3

C-2

C-1

-X

Solvent

17.5

21.6

CDCl3

12.5

29.0

CDCl3

12.6

29.3

CDCl3

14.1

22.8

30.5

36.3

CDCl3

14.1

22.8

31.9

27.7

38.1

CDCl3

R4-

22.9

31.9

29.7

33.0

CDCl3

Alkenyl Chemical Shifts

C-2

C-1

-X

Solvent

130.7

128.2

CDCl3

130.4

128.8

CDCl3

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The Sadtler Handbook of Proton NMR Spectra

116.5

136.0

CDCl3

113.5

137.0

CDCl3

115.6

137.4

CDCl3

115.0

137.7

115.5

137.8

CDCl3

137.8

138.6

CDCl3

114.3

139.2

97.0

141.5

CDCl3

97.2

141.6

CDCl3

114.4

143.1

CDCl3

110.7

146.5

CDCl3

109.0

149.8

CDCl3

86.1

152.3

-CH2-OH

CDCl3

-R4

CDCl3

-O-R4

CDCl3

Alkenyl Chemical Shifts

C-3

C-2

C-1

-X

Solvent

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The Sadtler Handbook of Proton NMR Spectra

112.3

143.2

21.8

CDCl3

112.0

144.9

22.0

CDCl3

109.7

146.0

22.4

-R9

CDCl3

109.9

146.0

22.4

-R5

CDCl3

108.8

147.5

22.3

-R2

CDCl3

E (CIS) Isomers

X-

C-2

C-1

-Y

Solvent

Br-

107.1

107.1

-Br

CDCl3

CH3-

123.9

130.7

-CH2CH2CH3

CDCl3

CH3-

123.7

131.0

-R5

CDCl3

135.2

135.2

CDCl3

Z (TRANS) Isomers

X-

C-2

C-1

-Y

Solvent

Br-

113.3

113.3 -Br

CDCl3

CH3-

124.9

131.6 -CH2CH2CH3

CDCl3

CH3-

124.6

131.8 -R5

CDCl3

R4-

130.6

130.6 -R4

CDCl3

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The Sadtler Handbook of Proton NMR Spectra

HO-N=CH-

N≡C-

134.7

134.7

CDCl3

126.0

137.6

CDCl3

116.3

137.7

Polysol

122.6

147.5 -CH3

CDCl3

131.8

148.8

CDCl3

96.4

150.3

CDCl3

121.2

152.0 -R3

CDCl3

131.1

152.3

CDCl3

133.3

158.2 -R3

CDCl3

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Unsaturated Hydrocarbons Alkynes

The alkynyl (C=C) carbons resonate in the chemical shift range from 68-92ppm. Because of their relatively long relaxation times, they tend to be "weak" peaks overlapping in many cases with the CDCI3 solvent bands. The alkynyl functional group has only a very weak deshielding effect on the C—1 and C—2 carbons (C1=+4.4ppm, C2=+6.0ppm). It displays a similar shielding effect on the alpha carbon of the alkynyl benzenes. The aromatic additivity constants are given below.

C-4

C-3

C-2

C-1

-X

0.3

-0.1

3.8

-6.0

H-C≡C-

-0.3

-0.2

3.2

-5.1

The chemical shifts of selected alkynyl compounds are presented in the following tables.

Alkyl Acetylenes: Alkyl Chemical Shifts

C-5

C-4

C-3

C-2

C-1

-C≡C-X

Solvent

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The Sadtler Handbook of Proton NMR Spectra

3.4

CDCl3

3.4

CDCl3

4.1

CDCl3

13.5

22.9

21.0

-C≡C-R5

CDCl3

13.7

22.1

30.9

18.3

-C≡C-H

CDCl3

14.0

22.4

31.3

29.1

18.6

-C≡C-R4

CDCl3

14.1

22.5

31.4

29.2

18.9

-C≡C-R3

CDCl3

R2-

31.4

28.6

27.7

18.7

R3-

29.1

29.4

29.1

18.9

-C≡C-CH3

CDCl3

R12-

29.3

29.0

28.8

18.5

-C≡C-H

CDCl3

CDCl3

Ethynylcyclohexane: Cyclohexyl Chemical Shifts

C-4 26.0

C-3,5 24.9

C-2,6 32.6

C-1

-X

Solvent

28.9

-C≡C-H

CDCl3

Alkynyl Benzenes; Phenyl Chemical Shifts

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The Sadtler Handbook of Proton NMR Spectra

C-4

C-3

C-2

C-1

-X

Solvent

128.7

128.3

132.2

122.4

-C≡C-H

CDCl3

129.1

128.4

132.4

121.8

127.6

128.3

131.7

124.4

128.1

128.2

131.6

123.3

CDCl3

CDCl3

-C≡C-CH3

CDCl3

Alkynyl Carbons Chemical Shifts

H-

C-2

C-1

-X

Solvent

H-

68.4 84.5

-R4

CDCl3

H-

68.2 84.4

-R12

CDCl3

H-

68.1 88.5

CDCl3

H-

77.4 83.8

CDCl3

CH3-

75.2 79.4

CH3-

75.6 78.9

CDCl3

CH3-

80.1 85.9

CDCl3

CH3-CH2-

81.9 79.2

CDCl3

R3-

80.0 80.4

-R5

CDCl3

R4-

80.0 80.0

-R4

CDCl3

-R7

CDCl3

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The Sadtler Handbook of Proton NMR Spectra

Alkynyl Benzenes; Alkynyl Chemical Shifts

X-

C-2

C-1

-X

Solvent

81.5

74.1

85.9

80.1

85.2

84.7

CDCl3

91.8

87.3

CDCl3

90.0

88.4

CDCl3

89.6

89.6

CDCl3

CDCl3

-CH3

CDCl3

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Aromatic Hydrocarbons Monocyclics and Polycyclics

This section contains the carbon-13 NMR chemical shifts of a selection of aromatic hydrocarbons. The chemical shifts of benzenes substituted by other than hydrocarbon groups are included in the section. As a substituent, the phenyl group exerts an intermediate deshielding effect on adjacent aliphatic carbon nuclei. Aliphatic additivity constants for the phenyl group are given below.

C-4

C-3

C-2

C-1

0.3

-2.5

8.8

22.0

The following tables provide aliphatic and aromatic chemical shifts for a selected variety of aromatic hydrocarbon compounds.

Alkyl Benzenes; Alkyl Carbon Chemical Shifts

C-6

C-5

C-4

C-3

C-2

C-1

-X

Solvent

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The Sadtler Handbook of Carbon NMR Spectra

R7-

298

21.43

CDCl3

15.6

29.1

CDCl3

14.4

22.6

33.8

35.9

CDCl3

29.8

29.6

31.6

36.1

CDCl3

Substituted Ethyl Benzenes; Ethyl Carbon Chemical Shifts

C-2

C-1

-X

Solvent

15.6

29.1

CDCl3

15.3

25.6

CDCl3

15.7

29.1

CDCl3

15.7

28.7

CDCl3

Phenyl Carbon Chemical Shifts Alkyl Benzenes

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The Sadtler Handbook of Carbon NMR Spectra

C-4

C-3

C-2

C-1

-X

Solvent

125.6

129.2

130.0

137.7

-CH3

CDCl3

125.7

128.4

127.9

144.2

-R2

CDCl3

125.7

128.5

128.3

142.6

-R3

CDCl3

125.6

128.4

128.4

142.9

-R17

CDCl3

126.0

128.4

128.4

140.0

CDCl3

125.9

129.3

128.8

141.0

CDCl3

125.9

128.5

128.5

141.5

CDCl3

125.9

128.4

128.4

141.9

CDCl3

125.7

128.3

128.3

142.1

CDCl3

125.8

128.3

127.0

147.5

CDCl3

125.8

128.4

126.4

148.8

CDCl3

126.2

129.4

128.2

143.8

CDCl3

125.9

131.2

127.5

146.8

CDCl3

Alkenyl Benzenes

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The Sadtler Handbook of Carbon NMR Spectra

C-4

C-3

C-2

C-1

-X

Solvent

127.8

128.5

126.2

137.7

CDCl3

128.7

128.7

126.5

137.3

CDCl3

125.5

128.8

128.0

138.8

CDCl3

127.4

128.2

125.6

141.4

CDCl3

128.2

128.2

127.7

141.6

CDCl3

125.5

128.5

128.0

138.8

CDCl3

C-4

C-3

C-2

C-1

127.1

128.7

127.1

141.2

Biphenyls

-X

Solvent CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

126.9

128.6

126.9

141.1

CDCl3

127.0

128.6

127.0

140.9

CDCl3

127.3

129.8

127.8

140.6

CDCl3

127.2

128.7

127.2

141.2

CDCl3

Alkynyl Benzenes

C-4

C-3

C-2

C-1

-X

Solvent

128.7

128.3

132.2

122.4

-C≡C-H

CDCl3

127.6

128.3

131.7

124.4

CDCl3

128.1

128.2

131.6

123.3

CDCl3

129.1

128.4

132.4

121.8

CDCl3

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Fluorinated Hydrocarbons Aliphatics

This section contains the carbon-13 NMR chemical shifts of fluorinated hydrocarbons. The chemical shifts of these compounds illustrate not only that fluorine is one of the most strongly deshielding substituents in its effect on the alpha carbon (alkanes: F-α C =+69.9ppm, benzenes: F-α C = +34.9ppm) but that fluorine 1 with I = /2, couples with nearby carbons through as many as four bonds. As the coupling constant tables indicate, the magnitude of J decreases with the increase in intervening bonds, i.e. F-α C > F-β C > F-δ C > F-σ C. In addition, the spectra of fluorobenzenes illustrate that coupling across substituted carbons or to substituted carbons tends to be smaller in magnitude than the corresponding coupling constant to or across carbons that possess bonded hydrogens. The following tables present the observed chemical shifts and coupling constant information for this group of compounds.

Fluorodecane

C-5

C-4

C-3

C-2

C-1

-F

Solvent

29.9

29.7

25.5

30.8

84.0

-F

CDCl3

Aliphatic Additivity Constants sigma

gamma

beta

alpha

-F

Solvent

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The Sadtler Handbook of Carbon NMR Spectra

0.2

-6.6

8.0

69.9

-F

CDCl3

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Fluorinated Hydrocarbons Aromatics

This section contains the carbon-13 NMR chemical shifts of fluorinated hydrocarbons. The chemical shifts of these compounds illustrate not only that fluorine is one of the most strongly deshielding substituents in its effect on the alpha carbon (alkanes: F-α C =+69.9ppm, benzenes: F-α C = +34.9ppm) but that fluorine with I = 1/2, couples with nearby carbons through as many as four bonds. As the coupling constant tables indicate, the magnitude of J decreases with the increase in intervening bonds, i.e. F-α C > F-β C > F-δ C > F-σ C. In addition, the spectra of fluorobenzenes illustrate that coupling across substituted carbons or to substituted carbons tends to be smaller in magnitude than the corresponding coupling constant to or across carbons that possess bonded hydrogens.

Fluorinated Aromatic Hydrocarbons

C-4

C-3

C-2

C-1

-X

Solvent

124.2

130.2

115.5

163.3

-F

CDCl3

132.1

129.0

125.5

131.5

-CF3

CDCl3

Aromatic Additivity Constants for Fluorine sigma

gamma

beta

alpha

-F

Solvent

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The Sadtler Handbook of Carbon NMR Spectra

-4.2

1.8

-12.9

34.9

-F

CDCl3

3.7

0.5

-3.0

2.7

-CF3

CDCl3

Selected Para-Substituted Fluorobenzenes

F-

C-4

C-3

C-2

C-1

-X

Solvent

F-

156.4 115.7

116.1

143.1

-NH2

CDCl3

F-

157.7 116.3

116.6

151.1

-OH

Polysol

F-

159.4 116.7

116.7

159.4

-F

CDCl3

F-

161.4 115.0

130.5

133.5

-CH3

CDCl3

F-

161.5 116.1

131.9

125.2

-SH

CDCl3

F-

161.7 116.8

130.2

129.5

-Cl

CDCl3

F-

161.9 117.2

132.5

116.7

-Br

CDCl3

F-

162.0 115.4

130.5

134.0

-CH2-CH2-Cl

CDCl3

F-

162.5 115.6

128.6

137.4

F-

165.2 116.9

134.8

108.8

F-

165.5 115.4

132.3

127.6

CDCl3

F-

165.8 115.7

131.1

133.9

CDCl3

F-

166.0 115.6

132.3

126.8

CDCl3

F-

166.7 116.6

126.6

144.9

CDCl3

CDCl3

-C≡N

Polysol

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The Sadtler Handbook of Carbon NMR Spectra

Fluorine-Carbon Coupling Constants

J19F-a = 4.9 Hz CDCl3 J19F-b =19.8 Hz CDCl3 J19F-c = 125.5 Hz CDCl3

J19F-a =125.5 Hz H2O J19F-b = 60.7 Hz H2O

J19F-CH2=16.9 Hz CDCl3

J19F-SO2-C= 22 Hz CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

J19F-SO2-C= 21.2 Hz CDCl3

2-Fluoropyridine

J19F-C2 = 239.2 Hz CDCl3 J19F-C3 = 36.7 Hz CDCl3 J19F-C4 = 7.3 Hz CDCl3 J19F-C5 = 4.8 Hz CDCl3 J19F-C6 = 14.5 Hz CDCl3

Fluorobenzene

J19F

C-1

C-2

C-3

245.7

21.7

7.3

C-4

C5

C-6

-H

7.3

21.7

C5

C-6

-X

Solvent

-H

Solvent CDCl3

Ortho-Substituted Fluorobenzenes J19F

C-1

C-2

C-3

238.3

14.7

6.4

17.0

-OH

CDCl3

244.1

17.5

6.3

23.3

-CH3

CDCl3

248.7

16.8

4.0

21.1

-Cl

CDCl3

249.1

16.7

7.4

22.0

-CH2-C≡N

CDCl3

7.0

C-4

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The Sadtler Handbook of Carbon NMR Spectra

254.1

12.6

8.8

24.2

CDCl3

Meta-Substituted Fluorobenzenes

J19F

C-1

C-2

C-3

241.7

24.4

244.2

C-4

C5

C-6

-X

Solvent

12.2

9.7

22.0

-NH2

CDCl3

23.6

11.7

10.0

21.1

-OH

CDCl3

246.2

22.3

7.3

7.9

21.7

246.6

22.0

7.3

7.3

26.8

249.1

24.4

7.4

7.3

19.5

CDCl3

249.1

24.4

7.3

22.0

CDCl3

C5

C-6

-X

Solvent

CDCl3

CDCl3

-CH2C≡N

Para-Substituted Fluorobenzenes

J19F

C-1

C-2

C-3

C-4

239.2

22.0

7.3

7.3

22.0

-OH

Polysol

242.3

21.1

7.3

7.3

21.2

-CH3

CDCl3

244.4

23.1

7.0

7.0

23.1

-SH

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

J19F

248.3

23.2

9.3

9.3

23.2

252.9

23.3

8.9

8.9

23.3

Polysol

255.1

21.4

9.4

9.4

21.4

CDCl3

256.1

23.6

11.1

11.1

23.6

CDCl3

256.3

23.3

9.1

9.1

23.3

C-1

C-2

291.1 Hz

35.1 Hz

3.5

3.5

C-3

-Br

-C≡N

CDCl3

CDCl3

Solvent CDCl3

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Chlorinated Hydrocarbons Aliphatics

This section contains selected chlorinated hydrocarbons. As a substituent in alkyl structures the chlorine atom possesses a moderately strong deshielding effect, i.e. Cl-α C = +30.6ppm. As a substituent on aromatic rings, chlorine has a weakly deshielding effect, i.e. Cl—α C=+6.0ppm.

1-Chloroalkanes

C-6

C-5

C-4

C-3

C-2

C-1

-Cl

Solvent

13.4

20.3

35.0

44.6

-Cl

CDCl3

14.0

22.8

31.4

26.9

33.0

44.9

-Cl

CDCl3

R2-

32.0

28.8

27.2

33.0

44.8

-Cl

CDCl3

2-Chlorobutane

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The Sadtler Handbook of Carbon NMR Spectra

C-4

C-3

C-2

C-1

-Cl

Solvent

11.1

33.6

25.0

60.1

-Cl

CDCl3

Chlorocyclopentane

C-3,5

C-2,4

C-1

-Cl

Solvent

23.2

37.3

61.8

-Cl

CDCl3

Chlorocyclohexane

C-4

C-3,5

C-2,6

C-1

-Cl

Solvent

25.4

25.0

36.9

59.9

-Cl

CDCl3

3-Chloropropene

C-3

C-2

C-1

-Cl

Solvent

118.3

134.3

45.1

-Cl

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

1,4-Dichloro-2-butene

Cl-

C-4

C-3

C-2

C-1

-Cl

Solvent

Cl-

43.7

130.2

130. 3

43.7

-Cl

CDCl3

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Chlorinated Hydrocarbons Aromatics

This section contains selected chlorinated hydrocarbons. As a substituent in alkyl structures the chlorine atom possesses a moderately strong deshielding effect, i.e. Cl-α C = +30.6ppm. As a substituent on aromatic rings, chlorine has a weakly deshielding effect, i.e. Cl—α C=+6.0ppm.

Chlorinated Aromatic Hydrocarbons

C-4

C-3,5

C-2,6

C-1

-X

Solvent

126.8 129.7 128.63 134.4

-Cl

CDCl3

128.2 128.6 128.6 137.5

-CH2-Cl

CDCl3

129.8 128.6 126.0 140.2

-CH-Cl2

CDCl3

130.1 128.1 125.3 144.1

-CCl3

CDCl3

127.5 129.5 127.5 145.2

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

4-Substituted Chlorobenzenes

Cl-

C-4

C-3

C-2

C-1

-X

Solvent

Cl-

122.8

129.0

116.3

145.2

-NH2

CDCl3

Cl-

126.2

129.7

116.9

153.6

-OH

CDCl3

Cl-

129.5

130.2

116.8

161.7

-F

CDCl3

Cl-

132.6

129.8

129.8

132.6

-Cl

CDCl3

Cl-

133.2

130.1

132.6

120.2

-Br

CDCl3

Cl-

134.1

130.3

138.6

91.1

-I

CDCl3

Cl-

138.1

128.5

131.5

135.7

Polysol

Cl-

138.3

128.5

131.1

129.8

Polysol

Cl-

139.3

129.6

133.4

111.0

Cl-

141.4

129.6

125.0

147.0

-C≡N

CDCl3 CDCl3

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Brominated Hydrocarbons Aliphatics

This section contains bromine containing hydrocarbons. As a substituent, bromine exerts a weakly deshieiding effect on the adjacent carbon atom. The aliphatic additivity constants for bromine are: Br-

C1=+19.4, C2 = +10.2, C3 = -3.8, C4 = -0.6 ppm

In aromatic molecules, bromine has the effect of actually shielding the C1 carbon atom. The aromatic additivity constants for bromine are: Br-

C1=-5.9, C2, 6 = + 3.0, C3, 5 = + 1.4, C4 = -1.7ppm

The tables shown below illustrate the chemical shifts of a selected variety of bromine containing organic compounds.

N-Alkyl Bromides

C-6

C-5

C-4

C-3

C-2

C-1

-Br

Solvent

19.5

27.5

-Br

CDCl3

13.0

26.5

35.5

-Br

CDCl3

13.2

21.5

35.0

33.1

-Br

CDCl3

13.9

22.0

30.5

32.8

33.4

-Br

CDCl3

14.0

22.7

31.2

28.1

33.1

33.4

-Br

CDCl3

R2-

31.7

28.5

28.2

33.0

33.7

-Br

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

R13-

29.9

29.0

28.4

33.2

33.2

-Br

CDCl3

Branched Alkyl Bromides 2-Bromobutane

C-4

C-3

C-2

C-1

-Br

Solvent

12.1

34.3

26.1

52.8

-Br

CDCl3

2-Bromopentane

C-5

C-4

C-3

C-2

C-1

-Br

Solvent

13.4

21.0

43.3

26.5

50.9

-Br

CDCl3

2-Bromohexane

C-6

C-5

C-4

C-3

C-2

C-1

-Br

Solvent

13.9

22.1

29.9

41.0

26.5

51.0

-Br

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

Alicyclic Bromides Bromocyclopentane

C-3,4

C-2,5

C-1

-Br

Solvent

23.4

38.0

53.0

-Br

CDCl3

Cyclohexanes

C-4

C-3,5

C-2,6

C-1

-X

Solvent

26.6

26.2

32.9

36.5

-CH2CH2Br

CDCl3

25.3.1

25.9

37.6

52.9

-Br

CDCl3

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Brominated Hydrocarbons Aromatics

This section contains bromine containing hydrocarbons. As a substituent, bromine exerts a weakly deshieiding effect on the adjacent carbon atom. The aliphatic additivity constants for bromine are: Br- C1=+19.4, C2 = +10.2, C3 = -3.8, C4 = -0.6 ppm In aromatic molecules, bromine has the effect of actually shielding the C1 carbon atom. The aromatic additivity constants for bromine are: Br- C1=-5.9, C2, 6 = + 3.0, C3, 5 = + 1.4, C4 = -1.7ppm

Aromatic Bromides

C-4

C-3,5

C-2,6

C-1

-X

Solvent

126.7

129.8

131.4

122.5

-Br

CDCl3

128.1

128.5

128.8

137.6

-CH2-Br

CDCl3

128.9

128.6

127.5

138.5

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

127.3

128.3

127.3

142.3

CDCl3

4-Substituted Bromobenzenes

Br-

C-1

C-2,6

C-3,5

C-4

-X

Solvent

Br-

106.9

131.8

113.4

146.7

Br-

109.8

131.9

116.7

145.6

-NH2

CDCl3

Br-

113.2

132.5

117.2

153.9

-OH

CDCl3

Br-

114.8

131.2

121.0

138.5

Br-

116.7

132.6

117.2

161.9

-F

CDCl3

Br-

119.1

131.2

130.7

136.5

-CH3

CDCl3

Br-

120.2

132.6

130.1

133.2

-Cl

CDCl3

Br-

121.0

133.0

133.0

121.0

-Br

CDCl3

Br-

121.4

132.2

129.3

135.7

Br-

122.1

133.3

139.0

91.9

Br-

127.1

131.5

131.2

130.2

Br-

127.8

132.5

133.3

111.2

Br-

127.8

131.6

131.1

129.5

CDCl3

Br-

127.8

131.8

129.5

136.0

CDCl3

CDCl3

Polysol

CDCl3

-I

CDCl3 Polysol

-C≡N

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

Br-

129.4

132.3

130.8

135.2

CDCl3

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Iodinated Hydrocarbons Aliphatics

The carbon-13 NMR chemical shifts of the iodinated hydrocarbons are distinguished by the unusually high field chemical shifts observed for carbon atoms bonded to the iodine substituent. These shifts appear as negative shifts resonating above TMS. CHI3

-146.5 ppm

CH2I2

~ 61.6 ppm

CH3I

- 22.5 ppm

The aliphatic additivity constants for iodine are: I-

C1 = -7.6,

C2 = +10.9,

C3 = -1.5,

C4 = -0.9 ppm

A similar shielding effect is noted in the spectra of the iodinated benzenes. The aromatic additivity constants for iodobenzenes are: I-

C1 = -34.1,

C2 = +8.6,

C3 = +1.4,

C4 = -1.4 ppm

Alkyl Iodides

C-5

C-4

C-3

C-2

20.6

C-1

-I

Solvent

-22.5

-I

CDCl3

-1.3

-I

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

15.3

26.9

9.2

-I

CDCl3

12.9

23.6

35.6

6.2

-I

CDCl3

13.8

21.6

32.7

33.2

6.5

-I

CDCl3

R2-

31.6

28.2

30.4

33.7

6.4

-I

CDCl3

R5-

29.5

28.6

30.5

33.7

6.5

-I

CDCl3

C-2

C-1

-I

Solvent

31.2

20.9

-I

CDCl3

C-3

C-2

C-1

-I

Solvent

22.5

30.3

18.1

-I

CDCl3

C-5

C-4

C-3

C-2

C-1

-I

Solvent

33.7

15.4

28.8

40.4

10.9

-I

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

I-

C-2

C-1

-I

Solvent

I-

3.0

3.0

-I

CDCl3

I-

C-3

C-2

C-1

-I

Solvent

I-

5.2

33.6

5.2

-I

CDCl3

I-

C-5

C-4

C-3

C-2

C-1

-I

Solvent

I-

6.7

32.9

29.0

32.9

6.7

-I

CDCl3

Alicyclic Iodides Cyclopentyl Iodide

C-3,4

C-2,5

C-1

-I

Solvent

23.9

39.8

28.1

-I

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

Cyclohexyl Iodide

C-4

C-3,5

C-2,6

C-1

-I

Solvent

25.2

27.1

39.5

32.0

-I

CDCl3

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Iodinated Hydrocarbons Aromatics

The carbon-13 NMR chemical shifts of the iodinated hydrocarbons are distinguished by the unusually high field chemical shifts observed for carbon atoms bonded to the iodine substituent. These shifts appear as negative shifts resonating above TMS. CHI3

-146.5 ppm

CH2I2

~ 61.6 ppm

CH3I

- 22.5 ppm

The aliphatic additivity constants for iodine are: I- C1 =

-7.6,

C2 = +10.9,

C3 = -1.5,

C4 = -0.9 ppm

A similar shielding effect is noted in the spectra of the iodinated benzenes. The aromatic additivity constants for iodobenzenes are: I-

C1 = -34.1,

C2 = +8.6,

C3 = +1.4,

C4 = -1.4 ppm

Iodinated Aromatic Hydrocarbons

C-4

C-3,5

C-2,6

C-1

-X

Solvent

127.0

129.8

137.1

94.3

-I

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

126.0

128.3

128.3

140.1

-(CH2)3-I

CDCl3

126.5

128.3

128.0

140.2

-CH2CH2-I

CDCl3

4-Substituted Iodobenzenes

I-

C-1

C-2

C-3

C-4

-X

Solvent

I-

76.8

137.1

116.7

147.4

-NH2

Polysol

I-

80.4

137.7

118.1

157.1

-OH

Polysol

I-

90.1

137.1

131.0

137.1

-CH3

CDCl3

I-

91.1

138.6

130.3

134.1

-Cl

CDCl3

I-

91.9

139.0

133.3

122.1

-Br

CDCl3

I-

93.0

137.7

128.8

139.8

I-

96.5

137.0

127.5

144.7

CDCl3

-SO2-OH

Polysol

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Primary Amines Aliphatics

This section contains the carbon-13 NMR chemical shifts of the primary amines. Other functional groups containing an -NH2 group include the hydrazines, amine salts and primary amides. The additivity effect of the primary amine group on adjacent aliphatic carbon atoms is that of a moderately strong deshielding group, i.e. H2N- C1 = + 28.3, C2 = + 11.3, C3 = -5.0, C4 = + 0.3ppm The aromatic additivity values of the aniline -NH2 are: H2N- C1 = + 18.3, C2 = - 13.3, C3 = + 0.8, C4 = - 10.2ppm Frequently the carbon-13 NMR spectra of primary amines display a singlet near 79 ppm which represents the resonance of chloroform that is formed by reaction with the solvent: -NH2 + CDCl3 → -NHD + CHCl3

Aliphatic Amines

C-3

C-2

C-1

-NH2

Solvent

11.3

27.1

44.3

-NH2

CDCl3

14.0

20.2

36.1

42.0

-NH2

CDCl3

14.1

22.8

29.5

33.9

42.5

-NH2

CDCl3

22.7

31.9

26.7

33.7

42.1

-NH2

CDCl3

C-5

14.0

C-4

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The Sadtler Handbook of Carbon NMR Spectra

R3-

29.5

29.7

27.2

34.0

42.3

-NH2

CDCl3

R5-

29.8

29.8

27.2

34.1

42.4

-NH2

CDCl3

tert-Butylamine

C-2

C-1

-NH2

Solvent

32.7

47.3

-NH2

CDCl3

2-Aminobutane

C-4

C-3

C-2

C-1

-NH2

Solvent

10.7

33.3

23.8

48.7

-NH2

CDCl3

3-Aminopentane

C-3

C-2

C-1

-NH2

Solvent

10.4

30.4

54.4

-NH2

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

2-Aminoheptane

C-5

C-4

C-3

C-2

C-1

-NH2

Solvent

32.2

26.3

40.6

24.2

47.2

-NH2

CDCl3

Alicyclic Amines Cyclopentylamine

C-3,4

C-2,5

C-1

-NH2

Solvent

24.0

36.3

53.4

-NH2

CDCl3

Cyclohexylamine

C-4

C-3,5

C-2,6

C-1

-NH2

Solvent

26.0

25.3

37.1

50.5

-NH2

CDCl3

Cycloheptylamine http://www.knowitall.com/handbook/cnmr/amines/primary/aliphatic/aliphatic.htm（第 3／4 页）2005-10-2 9:09:14

The Sadtler Handbook of Carbon NMR Spectra

C-4,5

C-3,6

C-2,7

C-1

-NH2

Solvent

28.4

24.3

38.8

52.8

-NH2

CDCl3

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Primary Amines Aromatics

This section contains the carbon-13 NMR chemical shifts of the primary amines. Other functional groups containing an -NH2 group include the hydrazines, amine salts and primary amides. The additivity effect of the primary amine group on adjacent aliphatic carbon atoms is that of a moderately strong deshielding group, i.e. H2N-

C1 = + 28.3, C

2 = + 11.3,

C3 = -5.0,

C4 = + 0.3ppm

The aromatic additivity values of the aniline -NH2 are: H2N-

C1 = + 18.3,

C2 = - 13.3,

C3 = + 0.8, C

4 = - 10.2ppm

Frequently the carbon-13 NMR spectra of primary amines display a singlet near 79 ppm which represents the resonance of chloroform that is formed by reaction with the solvent: -NH2 + CDCl3 → -NHD + CHCl3

Primary Aromatic Amines

C-4

C-3,5

C-2,6

C-1

126.9

128.9

128.2

139.0

-X

Solvent CDCl3

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The Sadtler Handbook of Proton NMR Spectra

126.1

128.2

126.3

139.0

CDCl3

126.0

128.7

128.3

140.0

CDCl3

126.6

128.3

127.0

143.4

-CH2-NH2

CDCl3

118.2

129.2

115.1

146.7

-NH2

CDCl3

126.6

128.3

125.7

148.0

CDCl3

4-Substituted Anilines

H2N-

C-1

C-2,6

C-3,5

H2N-

138.8

116.1

116.1

H2N-

139.6

115.7

H2N-

140.5

H2N-

C-4

Compound

Solvent

138.8

-NH2

Polysol

115.9

149.1

-OH

Polysol

116.3

114.9

152.6

-O-CH3

CDCl3

142.0

115.0

123.1

133.6

CDCl3

H2N-

142.7

116.1

121.0

148.5

CDCl3

H2N-

143.1

116.1

115.7

156.4

H2N-

143.9

114.9

125.8

140.9

H2N-

144.3

115.2

129.7

127.2

-CH3

CDCl3

H2N-

144.4

115.3

129.1

132.7

-R4

CDCl3

H2N-

144.6

115.3

127.0

138.7

-F

CDCl3 CDCl3

CDCl3

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The Sadtler Handbook of Proton NMR Spectra

H2N-

145.2

116.3

129.0

122.8

-Cl

CDCl3

H2N-

145.6

116.7

131.9

109.8

-Br

CDCl3

H2N-

147.4

116.7

137.1

76.8

-I

Polysol

H2N-

151.1

114.5

133.8

99.5

-C≡N

CDCl3

H2N-

153.1

113.2

131.4

117.2

Polysol

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Secondary Amines Aliphatics

This section contains the carbon-13 NMR chemical shifts of several types of secondary amine compounds (R’— NH— R"). The secondary amine groups exert a moderately strong deshielding effect on adjacent aliphatic carbons. Aliphatic additivity constants for the secondary amine groups are: R4-NH-

C1= + 36.3,

C2 = + 7.7,

C1= + 29.9,

C3 = - 4.4,

C2 = + 7.0,

C4 = + 0.4 ppm

C3 = - 4.7,

C4 = + 0.3 ppm

The additivity constants for the N-substituted anilines vary significantly in magnitude depending on the type of substituent bonded to the — NH— group: NH2-

C1= + 18.3,

C2 = -13.3,

C3 = + 0.8,

C4 = -10.2 ppm

C1= +14.7, C2 = -10.6, C3 = + 0.8, C4 = - 7.6 ppm R5-NHCH3-NH-

C1= + 20.2, C1= + 21.2,

C2 = -15.7, C2 = -16.0,

C3 = + 0.7, C3 = + 0.8,

C4 = - 11.4 ppm C4 = - 11.4 ppm

Aliphatic Secondary Amines

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The Sadtler Handbook of Carbon NMR Spectra

CH3

-NH-R

Solvent

29.4

-NH-R

Polysol

30.4

CDCl3

31.5

CDCl3

33.4

CDCl3

35.9

-NH-C6

CDCl3

36.3

-NH-R18

CDCl3

36.5

-NH-R4

CDCl3

C-6

C-5

C-4

13.9

C-3

C-2

C-1

-NH-R

14.8

38.3

CDCl3

14.8

38.7

CDCl3

15.9

41.2

15.3

43.6

CDCl3

11.8

23.3

51.4

CDCl3

11.9

23.6

52.3

20.3

31.7

43.6

-NH-C6

-NH-R3

http://www.knowitall.com/handbook/cnmr/amines/secondary/aliphatic/aliphatic.htm（第 2／3 页）2005-10-2 9:09:45

Solvent

CDCl3

CDCl3 CDCl3

The Sadtler Handbook of Carbon NMR Spectra

14.0

20.5

32.4

49.2

CDCl3

14.1

20.8

32.7

49.8

-NH-CH2CH3

CDCl3

14.1

20.7

32.6

50.0

-NH-R12

CDCl3

14.1

20.7

32.4

52.2

-NH-CH3

CDCl3

14.0

22.5

29.3

29.3

43.9

14.0

22.8

32.1

27.3

30.5

50.4

-NH-R6

CDCl3

R8-

29.9

29.9

27.7

30.5

50.4

-NH-R4

CDCl3

CDCl3

Secondary Cyclohexylamines

C-4

C-3,5

C-2,6

C-1

-NH-R

Solvent

26.0

25.1

33.4

51.5

26.5

25.4

34.6

53.2

-NH-C6

CDCl3

26.6

25.2

34.0

56.9

-NH-R2

CDCl3

26.5

25.2

33.3

58.7

-NH-CH3

CDCl3

CDCl3

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Secondary Amines Aromatics

This section contains the carbon-13 NMR chemical shifts of several types of secondary amine compounds (R’— NH— R"). The secondary amine groups exert a moderately strong deshielding effect on adjacent aliphatic carbons. Aliphatic additivity constants for the secondary amine groups are: R4-NH-

C1= + 36.3,

C2 = + 7.7,

C1= + 29.9,

C3 = - 4.4,

C2 = + 7.0,

C4 = + 0.4 ppm

C3 = - 4.7,

C4 = + 0.3 ppm

The additivity constants for the N-substituted anilines vary significantly in magnitude depending on the type of substituent bonded to the — NH— group: NH2-

C1= + 18.3, C

2 = -13.3,

C1= +14.7, R5-NHCH3-NH-

C1= + 20.2, C1= + 21.2,

C3 = + 0.8,

C2 = -10.6,

C2 = -15.7, C2 = -16.0,

C4 = -10.2 ppm

C3 = + 0.8,

C3 = + 0.7, C3 = + 0.8,

C4 = - 7.6 ppm

C4 = - 11.4 ppm C4 = - 11.4 ppm

Secondary Benzylamines

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The Sadtler Handbook of Carbon NMR Spectra

C-4

C-3,5

C-2,6

C-1

-X

Solvent

126.9

128.4

127.2

139.5

CDCl3

126.8

128.3

128.0

140.5

-CH2-NH-CH3

CDCl3

126.7

128.4

128.0

140.8

-CH2-NH-R2

CDCl3

-NH-R

Solvent

N-Substituted Anilines

C-4

C-3,5

C-2,6

C-1

128.1

128.1

119.0

141.4

Polysol

120.8

129.2

117.8

143.1

CDCl3

118.6

129.0

115.5

145.0

Polysol

118.0

128.9

115.8

145.8

Polysol

118.8

129.1

116.0

145.9

CDCl3

116.7

129.2

113.2

147.5

-NH-C6

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

116.9

129.3

113.4

147.7

CDCl3

117.3

129.1

112.7

148.1

CDCl3

117.0

129.1

112.7

148.6

-NH-R5

CDCl3

117.1

129.1

112.8

148.6

-NH-CH2CH3

CDCl3

117.0

129.2

112.4

149.6

-NH-CH3

CDCl3

4-Substituted Secondary Anilines

R-NH-

C-1

C-2,4

C-3,5

C-4

-X

Solvent

133.6

123.1

115.0

142.0

-NH2

CDCl3

134.5

121.8

114.6

152.3

-OH

Polysol

136.8

120.1

120.1

136.8

CH3-NH-

143.9

113.6

115.0

152.1

-O-CH3

CDCl3

R2-NH-

146.3

113.0

129.6

126.0

-CH3

CDCl3

CH3-NH-

147.4

112.5

129.7

125.9

-CH3

CDCl3

CH3-NH-

147.5

112.5

126.9

137.5

CDCl3

CH3-NH-

155.3

110.4

126.1

136.3

Polysol

Polysol

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The Sadtler Handbook of Carbon NMR Spectra

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Tertiary Amines Aliphatics

This section contains the carbon-13 NMR chemical shifts of selected tertiary amine and nitroso amine compounds. The tertiary amine groups exert a stronger deshielding effect on adjacent aliphatic carbons than the primary or secondary amine groups. A comparison of the aliphatic additivity constants follows: H2N-

C1= + 28.3,

CH3-NH- C1= + 37.9,

C2 = +11.3 C2 = + 6.7,

C1= + 46.0,

C3 = -5.0,

C4 = + 0.3 ppm

C3 = - 4.8,

C2 = + 4.9,

C4 = 0.0 ppm

C3 = -4.1,

C4 = + 0.3 ppm

A similar comparison is provided below to illustrate the deshielding/shielding properties of the primary, secondary and tertiary amine groups on the carbon resonances of benzene. The aromatic additivity constants are: H2N-

C1 = + 18.3,

CH3-HN- C1 = + 21.2,

C2 = -13.2, C2 = -16.0,

C1 = + 22.3,

C3 = + 0.8, C3 = + 0.8,

C2 = -15.7,

C4 = -10.2 ppm C4 = -11.4 ppm

C3 = + 0.6,

C4 = -11.8 ppm

The chemical shift data for a variety of tertiary amine compounds is presented in the following tables.

Alkyl Tertiary Amines

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The Sadtler Handbook of Carbon NMR Spectra

-N(R)2

C-1

Solvent

38.1

CDCl3

40.3

CDCl3

41.6

CDCl3

42.4

CDCl3

45.0

CDCl3

45.7

CDCl3

46.6

CDCl3

C-2

C-1

17.4

40.2

-N(R)2

Solvent CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

14.4

43.9

CDCl3

12.5

44.3

CDCl3

12.7

44.4

CDCl3

12.0

46.7

CDCl3

11.8

46.8

CDCl3

11.9

46.9

CDCl3

11.9

47.1

CDCl3

11.9

47.5

CDCl3

12.7

48.0

CDCl3

13.0

53.7

CDCl3

C-3

C-2

C-1

-N(R)2

Solvent

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The Sadtler Handbook of Carbon NMR Spectra

11.1

19.8

45.3

11.1

20.1

46.0

CDCl3

11.9

20.8

56.8

CDCl3

12.0

20.8

57.2

CDCl3

C-4

C-3

C-2

C-1

14.1

20.9

29.8

54.1

CDCl3

14.1

20.9

29.8

54.3

CDCl3

14.1

20.9

29.8

57.9

CDCl3

C-2,6

C-1

CDCl3

(SYN)

-N(R)2

Solvent

Cyclohexylamines

C-4

C-3,5

Solvent

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The Sadtler Handbook of Carbon NMR Spectra

26.6

26.6

32.0

58.2

CDCl3

26.7

26.5

29.7

60.0

CDCl3

26.6

25.9

29.2

63.9

CDCl3

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Tertiary Amines Aromatics

This section contains the carbon-13 NMR chemical shifts of selected tertiary amine and nitroso amine compounds. The tertiary amine groups exert a stronger deshielding effect on adjacent aliphatic carbons than the primary or secondary amine groups. A comparison of the aliphatic additivity constants follows: H2N-

C1= + 28.3,

CH3-NH-

C2 = +11.3

C1= + 37.9,

C1= + 46.0,

C3 = -5.0,

C4 = + 0.3 ppm

C2 = + 6.7, C

3 = - 4.8,

C4 = 0.0 ppm

C2 = + 4.9,

C3 = -4.1,

C4 = + 0.3 ppm

A similar comparison is provided below to illustrate the deshielding/shielding properties of the primary, secondary and tertiary amine groups on the carbon resonances of benzene. The aromatic additivity constants are: H2N-

C1 = + 18.3,

CH3-HN-

C2 = -13.2,

C1 = + 21.2,

C1 = + 22.3,

C3 = + 0.8,

C2 = -16.0,

C2 = -15.7,

C4 = -10.2 ppm

C3 = + 0.8,

C3 = + 0.6,

C4 = -11.4 ppm

C4 = -11.8 ppm

The chemical shift data for a variety of tertiary amine compounds is presented in the following tables.

Benzylamines

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C-4

C-3,5

C-2,6

C-1

-X

Solvent

126.7

128.4

126.7

138.9

CDCl3

126.9

128.1

127.8

139.1

CDCl3

126.7

128.6

128.1

139.9

CDCl3

Tertiary Anilines

C-4

C-3,5

C-2,6

C-1

-X

Solvent

119.6

129.2

126.8

136.7

125.4

129.4

120.2

140.7

CDCl3

127.1

129.3

119.0

142.3

CDCl3

119.6

129.6

127.3

142.5

CDCl3

CDCl3

(SYN)

(ANTI)

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The Sadtler Handbook of Carbon NMR Spectra

122.6

129.1

124.1

147.8

CDCl3

115.8

129.2

112.4

148.0

CDCl3

116.5

129.1

112.4

149.6

CDCl3

116.6

129.0

112.7

150.7

CDCl3

4-Substituted Tertiary Amines

C-1

C-2,6

C-3,5

C-4

-X

Solvent

144.0

115.3

115.3

144.0

149.0

113.2

129.6

125.8

149.3

1 13.1

126.9

129.8

149.5

114.1

131.7

108.5

150.1

112.4

125.9

125.9

CDCl3

153.1

110.6

131.1

117.4

Polysol

CDCl3

-CH3

CDCl3 CDCl3

-Br

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

153.3

110.7

131.2

117.3

CDCl3

C-1

C-2,6

C-3,5

C-4

-X

Solvent

146.0

112.8

129.8

124.7

-CH3

CDCl3

146.7

113.4

131.8

106.9

-Br

CDCl3

151.0

110.3

131.5

116.7

CDCl3

152.2

110.7

132.0

124.9

CDCl3

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Pyridines

This section contains the carbon-13 NMR chemical shifts of monosubstituted pyridines. The spectra display characteristically very low chemical shifts for positions 2 and 6 carbon nuclei. The chemical shift tables presented below contain a selected listing of carbon-13 resonances for a variety of pyridine compounds.

Alkyl Chemical Shifts

C-5

C-4

C-3

C-2

14.3

C-1

-Pyridine-R-

Solvent

17.9

CDCl3

23.7

CDCl3

24.3

CDCl3

23.6

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

14.0

22.6

C-2

C-1

30.3

34.4

31.8

15.3

26.1

CDCl3

14.3

28.2

CDCl3

29.5

14.2

CDCl3

-4-Pyridine

Solvent CDCl3

Pyridine Ring Carbon Chemical Shifts 2-Substituted Pyridines

C-6

C-5

C-4

C-3

C-2

-X

Solvent

151.2

128.8

137.4

127.3

133.8

-C≡N

CDCl3

150.1

122.7

138.5

128.2

142.1

-Br

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

149.2

127.0

137.6

124.8

148.4

Polysol

149.8

122.4

138.9

124.5

151.5

149.1

127.1

136.8

121.4

153.8

CDCl3

147.5

114.3

137.1

109.9

156.2

Polysol

149.5

122.1

136.9

123.5

156.9

CDCl3

149.6

122.0

136.6

120.3

157.3

CDCl3

147.7

111.4

136.9

105.7

159.3

CDCl3

147.6

112.6

137.3

108.5

159.7

-NH2

Polysol

141.1

120.2

135.0

105.7

163.8

-OH

Polysol

147.8

121.3

141.2

109.7

163.8

-F

CDCl3

147.1

116.6

138.3

111.1

164.4

-O-CH3

CDCl3

-X

Solvent

-Cl

CDCl3

3-Substituted Pyridines

C-6

C-5

C-4

C-3

C-2

147.8

125.0

143.9

93.6

155.6

153.4

123.6

135.4

132.5

149.9

138.9

123.9

121.3

143.7

137.2

152.7

123.2

137.0

132.9

150.9

-I

CDCl3 CDCl3

-NH2

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CDCl3 CDCl3

The Sadtler Handbook of Carbon NMR Spectra

147.8

124.7

138.5

120.8

151.0

-Br

CDCl3

149.6

123.3

135.2

139.2

147.3

-CH2-CH3

CDCl3

147.6

124.3

135.6

132.1

148.9

-Cl

CDCl3

139.9

122.7

124.1

154.3

138.1

-OH

Polysol

147.8

123.6

133.1

129.1

145.5

-CH=N-OH

Polysol

150.4

123.5

133.2

128.7

145.1

-CH=N-O-R3

CDCl3

147.3

123.3

134.0

133.2

150.1

CDCl3

4-Substituted Pyridines

C-4

C-3,5

C-2,6

-X

Solvent

150.8

121.3 142.9

CDCl3

150.3

122.8 144.3

CDCl3

149.5

123.9 149.5

CDCl3

149.8

124.0 149.8

CDCl3

149.6

120.6 159.5

CDCl3

149.8

123.4 152.8

-CH2-CH3

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

149.7

121.9 157.4

CDCl3

149.3

109.2 154.4

140.7

120.7 149.9

Polysol

139.5

120.8 150.1

CDCl3

-NH2

Polysol

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Amine Salts

The amine salts formed with inorganic acids display intermediate aliphatic chemical shifts similar in magnitude to those of the free amine forms. The aliphatic additivity constants are: Free amine

C1 = + 28.3,

C2 = + 11.3,

C3 = - 5.0ppm

Amine salt

C1 = + 26.1,

C2 = + 4.6,

C3 = - 5.6ppm

As with the free amine forms, the aliphatic primary amine salts resonate at higher fields than corresponding secondary amines and the secondary amine salts resonate at higher fields than the corresponding tertiary amine salts. 26.0ppm

35.7ppm

45.8ppm

Alkyl Amine Salts

C-6

C-5

C-4

C-3

C-2

C-1

-X

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Solvent

The Sadtler Handbook of Carbon NMR Spectra

26.0

D2O

35.7

D2O

45.8

D2O

47.4

D2O

13.3

36.3

H2O

11.5

42.8

D2O

9.5

47.6

H2O

11.2

20.8

41.4

Polysol

11.3

19.5

49.7

CDCI3

13.6

19.7

29.2

39.3

CDCI3

13.4

19.5

27.8

47.2

Polysol

13.5

20.3

27.8

44.6

CDCI3

14.0

22.5

31.3

26.5

27.6

40.3

CDCI3

R3-

29.1

29.1

23.5

27.0

52.7

CDCI3

Cyclobutylamine, Hydrochloride

C-3

C-2,4

C-1

Compound

Solvent

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The Sadtler Handbook of Carbon NMR Spectra

15.6

27.6

46.2

D2O

Cyclohexylamine Salts

-NH2(HX)

C-4

C-3

C-2

C-1

Solvent

24.8

24.2

30.4

50.1

Polysol

24.6

24.6

29.0

58.1

CDCI3

25.1

24.0

27.6

59.5

Polysol

Aniline Salts

-N(R)2(HX)

C-4

C-3,5

C-2,6

C-1

Solvent

130.1

131.0

123.8

131.0

D2O

128.9

129.7

123.2

135.9

Polysol

122.8

129.3

119.0

141.6

Polysol

124.8

130.6

116.5

144.3

D2O

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The Sadtler Handbook of Carbon NMR Spectra

125.6

129.2

122.2

145.8

Polysol

120.5

128.8

115.4

150.5

Polysol

N-Substituted Pyrrolidine Hydrochlorides

-NH2(HX)

Solvent

C-3,4

C-2,5

23.3

52.8

D2O

22.1

56.8

Polysol

Substituted Pyridine Salts

C-6

C-5

C-4

C-3

C-2

149.5

131.7

143.6

128.8

141.3

Compound

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Solvent D2O

The Sadtler Handbook of Carbon NMR Spectra

149.0

128.6

143.0

128.3

151.1

D2O

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Oximes

This section contains the chemical shifts of the oximes and derivatives which contain the -CH=N- group. The carbon-13 spectra usually display resonance bands for both the syn- and anti- forms. The oxime -CH=N- resonance is found in the chemical shift range from 137 to 158 ppm depending upon its environment.

Alkyl Chemical Shifts

C-3

C-2

C-1

-CH=N-OH

Solvent

11.1

147.9 (syn)

CDCl3

15.0

148.2 (anti)

CDCl3

13.9

19.5

27.1

152.5 (syn)

CDCl3

13.5

20.1

31.5

152.1 (anti)

CDCl3

Alkenyl Chemical Shifts

CH=

CH

-CH=N-OH

Solvent

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The Sadtler Handbook of Carbon NMR Spectra

137.7

116.3

147.2

Polysol

Aromatic Chemical Shifts

C-4

C-3,5

C-2,6

C-1

-CH=N-OH

Solvent

130.0

128.7

127.2

131.9

150.6

CDCl3

Chemical Shifts of the –CH=N-OH Group HO-N=CH

-R

Solvent

137.1

CDCl3

(syn) CDCl3

140.3

(anti) 144.0

Polysol

146.4

Polysol

146.8

CDCl3

147.2

Polysol

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The Sadtler Handbook of Carbon NMR Spectra

147.7

CDCl3

147.9 -CH3 (syn)

CDCl3

148.2 -CH3 (anti)

CDCl3

149.3

Polysol

149.8

Polysol

150.3

CDCl3

150.6

CDCl3

152.0

CDCl3

(syn) 152.5

CDCl3

(anti) 152.6

CDCl3

156.7

CDCl3

(anti) 157.6

CDCl3

(syn)

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Quaternary Ammonium Salts

The carbon-13 NMR chemical shifts of the quaternary ammonium compounds contained in this section display the strongly deshielding effect of the N(+) group. Additionally, they illustrate the spin-spin coupling that exists between Nitrogen-14 and adjacent carbon atoms. With methyl groups (N(+ - CH3), the coupling may result in the formation of a narrow triplet (J = 3.5Hz) for the -CH3 resonance. In other cases, the coupling is too narrow to be resolved resulting in only a distinctly broadened resonance for the adjacent carbon nuclei.

Alkyl Chemical Shifts

C-5

C-4

C-3

C-2

C-1

-X

Solvent

52.4

CDCI3

53.4

CDCI3

56.2

H2O

57.0

Polysol

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The Sadtler Handbook of Carbon NMR Spectra

7.4 51.9

Polysol

8.6 53.0

CDCI3

10.7 54.2

CDCI3

8.7 56.9

CDCI3

11.0

16.1 60.9

CDCI3

10.7

15.4 59.8

CDCI3

13.6

19.4

23.6 58.0

Polysol

13.5

19.6

23.8 58.5

CDCI3

R10-

28.7

25.6

31.5 60.8

Polysol

R12-

29.8

26.2

32.0 62.1

CDCI3

R8-

29.3

26.2

23.2 66.8

CDCI3

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The Sadtler Handbook of Carbon NMR Spectra

Aromatic Chemical Shifts Benzyl Ammonium Salts

C-4

C-3

C-2

C-1

CH2

130.4

129.1

132.6

127.4

CH2

CDCI3

130.5

129.0

133.1

127.9

CH2

CDCI3

-X

Solvent

Phenyl Ammonium Salts

C-4

C-3,5

C-2.6

C-1

-X

Solvent

130.3

130.7

122.7

141.0

CDCI3

130.2

130.2

119.6

146.2

Polysol

131.5

131.5

120.8

147.6

D2O

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The Sadtler Handbook of Carbon NMR Spectra

C-4

C-3,5

C-2,6

-X

Solvent

145.6

128.3

145.1

Polysol

146.9

129.1

145.5

D2O

145.3

128.7

145.6

CDCI3

147.6

128.9

146.7

D2O

Coupling Constants (14N-CH3)

3.5 Hz H2O

4.8 Hz D2O

4.9 Hz D2O

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Nitriles Aliphatics

The carbon-13 NMR chemical shifts of the carbonitrile compounds contained in this section display the characteristically weak resonance of the C≡N carbon over the chemical shift range from 111 to 126 ppm. The long relaxation time exhibited by the nitrile carbon often requires the utilization of relatively small pulse widths and/or the addition of a relaxation agent to the sample solution. The C≡N group exerts a very weakly deshielding effect on the adjacent aliphatic carbon and a strongly shielding effect on C-1 of aromatic ring systems. The aliphatic additivity constants for the nitrile groups are: N≡C-

C1= + 3.0,

C2 = + 2.8,

C3 = -3.3,

C4 = 0.0 ppm

The tables presented below illustrate the chemical shifts of a variety of selected nitrile compounds.

Alkyl Chemical Shifts

C-6

R4-

C-5

C-4

C-3

C-2

C-1

-C≡N

Solvent

1.7

117.4

CDCl3

10.9

10.6

121.0

CDCl3

13.2

19.0

19.4

119.8

CDCl3

13.2

22.0

27.6

16.7

119.9

CDCl3

13.8

22.0

31.0

25.4

17.1

119.7

CDCl3

29.7

29.5

28.9

25.6

17.1

119.6

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

R9-

29.8

29.5

28.8

25.6

17.1

119.5

Alicyclic Carbonitriles Cyclopropanecarbonitrile

C-2,3

C-1

-C≡N

Solvent

7.1

-3.5

122.3

CDCl3

Cyclohexanecarbonitrile

C-4

C-3,5

C-2,6

C-1

-C≡N

Solvent

25.4

24.2

29.7

28.1

122.4

CDCl3

Chemical Shifts of the -C≡N Group N≡C-

-x

Solvent

111.7

Polysol

112.9

CDCl3

113.7

CDCl3

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CDCl3

The Sadtler Handbook of Carbon NMR Spectra

114.5

CDCl3

114.8

Polysol

115.9

CDCl3

117.1

CDCl3

117.4

-CH3

CDCl3

118.3

CDCl3

118.8

CDCl3

119.7

CDCl3

119.9

-R4

CDCl3

121.0

CDCl3

122.3

CDCl3

122.4

CDCl3

123.9

CDCl3

125.6

CDCl3

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Nitriles Olefinics

The carbon-13 NMR chemical shifts of the carbonitrile compounds contained in this section display the characteristically weak resonance of the C≡N carbon over the chemical shift range from 111 to 126 ppm. The long relaxation time exhibited by the nitrile carbon often requires the utilization of relatively small pulse widths and/or the addition of a relaxation agent to the sample solution. The C≡N group exerts a very weakly deshielding effect on the adjacent aliphatic carbon and a strongly shielding effect on C-1 of aromatic ring systems. The aliphatic additivity constants for the nitrile groups are: N≡C- C1= + 3.0, C2 = + 2.8, C3 = -3.3, C4 = 0.0 ppm

Alkenyl Nitriles

C-3

C-2

C-1

-C≡N

Solvent

24.2

29.7

28.1

122.4

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

CH2=

C(CH3)

-C≡N

Solvent

131.2

118.5(20.6)

119.3

CDCl3

CH2=

C(Cl)

-C≡N

Solvent

131.8

110.8

114.5

CDCl3

C-2

C-1

-C≡N

Solvent

150.3

96.4

118.3

CDCl3

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Nitriles Aromatics

The carbon-13 NMR chemical shifts of the carbonitrile compounds contained in this section display the characteristically weak resonance of the C≡N carbon over the chemical shift range from 111 to 126 ppm. The long relaxation time exhibited by the nitrile carbon often requires the utilization of relatively small pulse widths and/or the addition of a relaxation agent to the sample solution. The C≡N group exerts a very weakly deshielding effect on the adjacent aliphatic carbon and a strongly shielding effect on C-1 of aromatic ring systems. The aromatic additivity constants for this group are: N≡C- C1=-16.0, C2,6 = + 3.7, C3,5 = + 0.8, C4 = + 4.4ppm The tables presented below illustrate the chemical shifts of a variety of selected nitrile compounds.

Aromatic Niltriles

C-4

C-3,5

C-,6

C-1

-R

Solvent

-C≡N

CDCl3

132.8

129.2

132.1

112.4

127.9

127.9

129.0

130.5

CDCl3

127.2

129.4

127.2

132.5

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

131.1

127.4

129.0

133.5

CDCl3

128.1

129.1

127.6

136.1

CDCl3

128.8

128.4

127.1

138.5

CDCl3

4-Substituted Benzonitriles

N≡C-

C-1

C-2,6

C-3,5

117.0

116.2

132.9

132.9

117.9

111.2

133.3

117.8

116.4

118.1

C-4

-x

Solvent

116.2

-C≡N

Polysol

132.5

127.8

-Br

CDCl3

133.3

126.5

134.2

-CF3

Polysol

115.5

132.2

130.0

135.1

117.8

111.0

133.4

129.6

139.3

-Cl

CDCl3

119.0

109.5

131.9

130.0

143.7

-CH3

CDCl3

118.8

111.0

132.5

129.1

145.6

120.5

99.5

133.8

114.5

151.1

-NH2

CDCl3

119.6

101.9

134.0

116.5

161.4

-OH

Polysol

118.0

108.8

134.8

116.9

165.2

-F

CDCl3

Polysol

CDCl3

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Thiocyanates

The thiocyanate group (S-C≡N) exerts a relatively weak chemical effect on adjacent aliphatic carbon atoms. The aliphatic additivity constants for the thiocyanate group are shown below. N≡C-S-

C1=+20.0,

C2=+6.7,

C3=-4.1,

C4=-0.5 ppm.

The carbon resonance of the S-C≡N group of thiocyanate esters absorbs over a narrow chemical shift range from 110 - 114 ppm compared to 111 - 126 ppm for the nitrile (R-C≡N) group. The thiocyanate salts show a C≡N resonance near 133 ppm in D2O solution. A selection of thiocyanate chemical shifts are show in the tables presented below.

Alkyl Thiocyanates

C-5

R7-

C-4

C-3

C-2

C-1

-S-C≡N

Solvent

16.5

113.4

CDCl3

15.4

28.7

112.1

CDCl3

13.8

22.1

30.1

29.7

34.1

112.1

CDCl3

29.5

29.0

28.0

29.5

34.1

111.7

CDCl3

Isopentyl Thiocyanate

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The Sadtler Handbook of Proton NMR Spectra

C-4

C-3

C-2

C-1

-S-C≡N

Solvent

22.0

26.9

38.8

32.2

112.0

CDCl3

Benzyl Thiocyanate

C-4

C-3,5

C-2,6

C-1

CH2-

-S-C≡N

Solvent

128.7

128.9

128.9

134.6

37.9

112.0

CDCl3

Chemical Shifts of the (S-C≡N) Group

C-1

-X

110.9

111.7

Solvent CDCl3

-R12

CDCl3

112.0

CDCl3

112.0

CDCl3

112.1

-R5

CDCl3

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The Sadtler Handbook of Proton NMR Spectra

112.8

CDCl3

113.4

-CH3

CDCl3

Thiocyanate Salts

C-1

-X

Solvent

132.9

-K

D2 O

133.4

-NH4

D2O

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Nitro Compounds Aliphatics

As the carbon-13 NMR chemical shifts in this section illustrate, the - NO2 group has a strongly deshielding effect on the adjacent carbon (C-1) of both aliphatic and aromatic compounds. The additivity constants for nitrobenzenes are: NO2-

C1= + 19.9,

C2 = -4.9,

C3 = +1.1,

C4 = + 6.4ppm

The C-1 carbons of the nitrobenzenes tend to have an abnormally long relaxation time requiring short pulse widths and/or the addition of relaxation agents.

Nitro Alkanes

C-1

-NO2

Solvent

63.0

-NO2

CDCl3

C-2

C-1

-NO2

Solvent

12.4

70.9

-NO2

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

C-2

C-1

-NO2

Solvent

20.8

79.2

-NO2

CDCl3

C-2

C-1

-NO2

Solvent

27.8

85.2

-NO2

CDCl3

Nitrocyclohexane

C-4

C-3,5

C-2,6

C-1

-NO2

Solvent

25.2

24.4

31.3

84.8

-NO2

CDCl3

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Nitro Compounds Aromatics

As the carbon-13 NMR chemical shifts in this section illustrate, the - NO2 group has a strongly deshielding effect on the adjacent carbon (C-1) of both aliphatic and aromatic compounds. The additivity constants for nitrobenzenes are: NO2-

C1= + 19.9,

C2 = -4.9,

C3 = +1.1,

C4 = + 6.4ppm

The C-1 carbons of the nitrobenzenes tend to have an abnormally long relaxation time requiring short pulse widths and/or the addition of relaxation agents.

Aromatic Nitro Compounds

C-4

C-3,5

C-2,6

C-1

-X

Solvent

128.3

128.7

128.3

131.1

CDCl3

134.8

129.5

123.5

148.5

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

4-Substituted Nitrobenzenes

C-1

C-2,6

C-3,5

C-4

-X

Solvent

NO2-

150.6

123.5

130.7

136.1

NO2-

147.0

125.0

129.6

141.4

NO2-

150.4

123.7

129.4

141.7

NO2-

147.5

123.8

129.8

144.9

-CH2-CI

CDCl3

NO2-

146.4

123.5

129.9

146.1

-CH3

CDCl3

NO2-

136.9

126.3

112.8

155.1

-NH2

CDCl3

NO2-

136.3

126.1

110.4

155.3

-NH-CH3

CDCl3

NO2-

141.4

125.8

114.5

164.3

-O-CH2CH3

CDCl3

NO2-

140.9

126.6

116.3

164.5

-OH

CDCl3

NO2-

144.9

126.6

116.6

166.7

-F

CDCl3

CDCl3

-Cl

CDCl3 CDCl3

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Phosphorus Compounds

The carbon-13 NMR chemical shifts of organic compounds containing phosphorus characteristically display 31P - 13C coupling across as many as 4 intervening bonds. The chemical shift effect exerted by all of the different valence states in which phosphorus can exist varies from that of a weakly deshielding substituent on adjacent aliphatic carbons to either a weakly shielding or weakly deshielding substituent on aromatic phenyl C-1 carbons. The aliphatic additivity constants for compounds in this group are:

C1= + 13.5,

C2 = + 3.0,

C1= + 17.0,

C3 = + 0.6,

C2 = -0.7,

C4 = - 0.4ppm

C3 = -1.4,

C4 = - 0.6ppm

The aromatic additivity constants are:

C1=-10.9,

C2, 6 = + 6.0,

C3, 5 = + 2.1

C4 = + 7.1ppm

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The Sadtler Handbook of Carbon NMR Spectra

C1= + 5.3,

C2, 6 = + 3. 5,

C3, 5 = 0.0,

C4 = + 3.2ppm

The tables that are presented below illustrate the chemical shifts and coupling constants for a variety of phosphorus containing organic molecules.

Alkyl Chemical Shifts

-P(R)n

C-1

Solvent

5.8

CDCl3

12.4

CDCl3

-P(R)n

Solvent

C-2

C-1

7.6

10.0

CDCl3

5.6

11.0

Polysol

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The Sadtler Handbook of Carbon NMR Spectra

6.9

17.0

CDCl3

6.6

19.1

CDCl3

9.9

20.5

CDCl3

C-3

C-2

C-1

15.5

15.7

21.3

CDCl3

15.2

15.6

22.7

CDCl3

C-4

C-3

C-2

-P(R)n

C-1

Solvent

-P(R)n

Solvent

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The Sadtler Handbook of Carbon NMR Spectra

13.7

23.6

24.5

22.7

CDCl3

13.6

24.8

23.1

26.2

CDCl3

13.8

27.9

24.6

27.8

CDCl3

Rn-

C-4

C-3

C-2

C-1

R4-

29.4

31.7

26.1

27.6

CDCl3

R8-

29.3

29.1

22.3

30.5

CDCl3

R4-

29.2

30.9

22.5

31.1

CDCl3

-P(R)n

Allyl Phosphorus Compounds

C-3

C-2

C-1

-P(R)n

Solvent

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Solvent

The Sadtler Handbook of Carbon NMR Spectra

123.2

126.2

28.9

CDCl3

125.3

124.1

21.7

CDCl3

Vinyl Chemical Shifts

C-2

C-1

135.1

126.8

-P(R)n

Solvent CDCl3

Phenyl Group Chemical Shifts

C-4

C-3

C-2

C-1

-P(R)n

Solvent

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The Sadtler Handbook of Carbon NMR Spectra

135.5

130.5

134.4

117.5

Polysol

135.1

130.6

133.6

117.9

CDCl3

135.1

130.6

133.5

118.2

CDCl3

131.6

128.5

131.9

132.8

Polysol

131.6

128.4

131.9

133.7

CDCl3

131.2

128.0

130.5

134.1

Polysol

134.7

129.3

130.1

134.3

CDCl3

131.5

129.2

131.7

138.6

NaOD

133.2

128.9

131.2

142.9

CDCl3

128.6

128.4

133.6

137.2

CDCl3

128.4

128.3

132.6

138.5

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

130.1

128.4

131.6

138.6

CDCl3

128.4

128.2

132.0

140.1

CDCl3

Aliphatic Coupling Constants (31P-13C) -31P(R)n

C-1

Solvent

14.0 Hz

CDCl3

50.7 Hz

CDCl3

-31P(R)n

C-2

C-1

16.4 Hz

10.0 Hz

CDCl3

5.9 Hz

47.6 Hz

Polysol

Solvent

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The Sadtler Handbook of Carbon NMR Spectra

4.8 Hz

51.3 Hz

CDCl3

6.6 Hz

144.1 Hz

CDCl3

C-3

C-2

C-1

13.4 Hz

14.4 Hz

11.9 Hz

CDCl3

7.7 Hz

11.5 Hz

33.5 Hz

CDCl3

14.6 Hz

4.9 Hz

46.8 Hz

CDCl3

12.0 Hz

4.2 Hz

48.5 Hz

CDCl3

14.6 Hz

3.9 Hz

50.4 Hz

CDCl3

16.2 Hz

4.5 Hz

53.0 Hz

CDCl3

-31P(R)n

Solvent

Alkenyl Coupling Constants (31P-13C)

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The Sadtler Handbook of Carbon NMR Spectra

C-2

C-1

-X

Solvent

183.1 Hz

CDCl3

C-3

C-2

C-1

9.7 Hz

13.0 Hz

49.6 Hz

-X

Solvent CDCl3

Phenyl Coupling Constants (31P-13C)

-P(R)n

Solvent

C-3 Hz

C-2 Hz

C-1 Hz

6.8

19.5

11.9

CDCl3

6.5

15.9

12.0

CDCl3

5.0

18.7

12.8

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

5.5

24.2

33.3

CDCl3

12.3

9.8

85.5

CDCl3

12.2

9.9

86.4

CDCl3

13.7

9.7

89.4

Polysol

14.7

12.2

85.4

Polysol

18.3

14.5

117.4

CDCl3

12.1

8.9

63.2

CDCl3

14.4

9.8

118.4

Polysol

11.8

8.9

131.3

NaOD

14.1

12.2

141.6

CDCl3

21.5

16.9

155.1

CDCl3

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Sulfides Aliphatics

This section contains the carbon-13 NMR chemical shifts of the alkyl and aromatic sulfides and the thiophenes. As expected, the deshielding effect of the various sulfide groups on the adjacent carbon is significantly stronger than that of the thiols. A comparison of their additivity constants is shown below. The aliphatic additivity constants are: HS-

C1=+10.5,

C2- + 11.4,

C1=+18.7, CH3-S-

C1= + 20.4,

C3 = -3.6,

C2 = + 9.2,

C2 = + 6.2,

C4 = - 0.2 ppm

C3 = -4.1,

C3 = -2.7,

C4 = 0.0 ppm

C4 = + 0.3 ppm

The assignment of thiophene resonances based on chemical shifts is complicated by the fact that the chemical shift of C-2 and C-5 is very similar to that of C-3 and C-4 (125.0 vs. 126.7 ppm). In general, it is found that there is a rough correlation between a substituent's shielding effect on benzene carbon atoms and its effect on the corresponding thiophene ring positions.

Alkyl Sulfides

C-6

C-5

C-4

C-3

C-2

C-1

-S-R

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Solvent

The Sadtler Handbook of Carbon NMR Spectra

14.7

CDCl3

15.5

-S-R12

CDCl3

15.6

CDCl3

14.3

25.1

CDCl3

14.9

25.6

-S-R2

CDCl3

14.1

26.1

-S-R4

CDCl3

14.2

26.7

CDCl3

13.7

22.2

32.2

32.2

-S-R4

CDCl3

14.1

22.7

31.7

28.8

29.9

32.4

-S-R6

CDCl3

R2-

31.9

29.1

29.1

29,9

32.4

-S-R7

CDCl3

R11-

29.4

29.1

28.7

31.6

32.8

R7-

29.8

29.8

29.4

29.0

34.5

Polysol

-S-CH3

Alkyl Group Chemical Shifts

C-3

13.7

C-2

C-1

-2-Thiophene

Solvent

14.9

CDCl3

16.1

23.7

CDCl3

25.1

32.0

CDCl3

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CDCl3

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Sulfides Aromatics

This section contains the carbon-13 NMR chemical shifts of the alkyl and aromatic sulfides and the thiophenes. As expected, the deshielding effect of the various sulfide groups on the adjacent carbon is significantly stronger than that of the thiois. A comparison of their additivity constants is shown below. The aliphatic additivity constants are: HS-

C1=+10.5,

C2- + 11.4,

C1=+18.7, CH3-S-

C1= + 20.4,

C3 = -3.6,

C2 = + 9.2,

C2 = + 6.2,

C4 = - 0.2 ppm

C3 = -4.1,

C3 = -2.7,

C4 = 0.0 ppm

C4 = + 0.3 ppm

The assignment of thiophene resonances based on chemical shifts is complicated by the fact that the chemical shift of C-2 and C-5 is very similar to that of C-3 and C-4 (125.0 vs. 126.7 ppm). In general, it is found that there is a rough correlation between a substituent's shielding effect on benzene carbon atoms and its effect on the corresponding thiophene ring positions.

Benzyl Sulfides

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The Sadtler Handbook of Carbon NMR Spectra

C-4

C-3,5

C-2,6

C-1

-CH2-

126.9

129.5

128.3

137.3

38.7

CDCl3

127.3

129.3

128.4

137.3

43.2

CDCl3

126.9

128.8

128.4

138.4

38.3

-S-CH3

CDCl3

126.7

128.8

128.3

138.6

35.8

-S-R2

CDCl3

-S-R

Solvent

Phenyl Sulfides

C-4

C-3,5

C-2,6

C-1

-S-R

126.8

128.9

130.8

135.7

CDCl3

126.0

128.7

128.3

136.5

CDCl3

124.9

128.7

126.7

138.6

C-3

C-2

Solvent

125.0

CDCl3

-S-CH3

Solvent

CDCl3

Thiophene

C-5 125.0

C-4 126.7

126.7

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The Sadtler Handbook of Carbon NMR Spectra

2-Substituted Thiophenes

C-4

C-3

C-2

C-1

-X

Solvent

131.0

128.4

136.4

73.2

-I

CDCl3

133.1

127.9

137.6

109.6

-C≡N

CDCl3

124.0

126.0

126.5

130.1

-Cl

CDCl3

132.3

127.8

133.3

134.9

Polysol

129.9

127.7

127.7

138.0

Polysol

125.1

126.6

123.9

142.9

CDCl3

131.7

128.2

133.2

144.3

CDCl3

122.8

126.6

124.1

145.3

-R3

CDCl3

Alkyl Group Chemical Shifts

C-3

13.7

C-2

C-1

-2-Thiophene

Solvent

14.9

CDCl3

16.1

23.7

CDCl3

25.1

32.0

CDCl3

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Disulfides

The chemical shift effect of the disulfide functional group displayed by the carbon-13 NMR chemical shifts in this section is that of a moderately strong deshielding substituent in relation to adjacent aliphatic carbons. A comparison of the aliphatic additivity constants for the sulfide and disulfide groups is given below. The aliphatic additivity constants are: R-S-S- C1= + 25.2, C2 = + 6.6, C3 = - 3.4, C4 = -0.1 ppm R-S- C1=+17.9, C2 = + 7.1, C3 = -3.0, C4 = -0.1 ppm A similar moderately strong deshielding effect is noted in the chemical shift of aromatic C-1's. The aromatic additivity constants are:

C1= + 7.5,

C2,6 = -1.0,

C3, 5 = + 0.4,

C4 = -1.5 ppm

The following tables contain representative chemical shifts for a variety of disulfide compounds.

Alkyl Disulfides

C-6

C-5

C-4

C-3

13.1

C-2

C-1

-S-S-R

Solvent

22.2

-S-S-CH3

CDCl3

14.5

33.0

-S-S-R2

CDCl3

22.6

41.2

-S-S-R3

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

R5-

13.7

21.7

31.4

38.9

-S-S-R4

CDCl3

13.9

22.4

30.8

29.1

39.4

-S-S-R5

CDCl3

29.7

29.4

28.7

29.4

39.3

-S-S-R10

CDCl3

tert-Butyl Disulfide

C-2

C-1

30.5

45.8

-S-S-R

Solvent CDCl3

Isobutyl Disulfide

C-3

C-2

C-1

21.8

28.3

48.7

-S-S-R

Solvent CDCl3

sec-Butyl Disulfide

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The Sadtler Handbook of Carbon NMR Spectra

C-4

C-3

C-2

C-1

11.5

29.1

20.2

48.2

-S-S-R

Solvent CDCl3

Isopentyl Disulfide

C-4

C-3

C-2

C-1

22.3

27.2

37.2

38.4

-S-S-R

Solvent CDCl3

Aromatic Disulfides

C-4

C-3

C-2

C-1

-R

127.2

129.3

128.3

137.3

CDCl3

126.9

128.8

127.4

136.9

CDCl3

CH3-

127.1

129.6

128.5

133.9

CDCl3

Br-

121.4

132.2

129.3

135.7

Polysol

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Solvent

The Sadtler Handbook of Carbon NMR Spectra

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Thiols Aliphatics

The spectra of the thiol containing compounds in this section indicate that the -SH group exerts a very weak deshielding effect on both aliphatic and aromatic position 1 carbons. The aliphatic additivity constants are: HS-

C1=+10.5,

C2 = + 11.4,

C3 = -3.6,

C4 = - 0.2 ppm

The aromatic additivity constants are: HS-

C1= + 2.3,

C2, 6 = + 0.9,

C3, 5 = + 0.5,

C4 = -3.0 ppm

A selection of thiol chemical shifts is presented in the tables below.

N-Alkyl Thiols

C-6

C-5

C-4

C-3

C-2

C-1

-SH

Solvent

19.7

19.1

-SH

CDCl3

13.5

21.6

36.3

24.3

-SH

CDCl3

14.1

22.7

31.5

28.2

34.3

24.7

-SH

CDCl3

R4-

29.7

29.4

28.6

34.3

24.6

-SH

CDCl3

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The Sadtler Handbook of Proton NMR Spectra

R13-

29.8

29.2

28.5

34.2

24.6

-SH

CDCl3

Cyclohexanethiol

C-4

C-3,5

C-2,6

C-1

-SH

Solvent

25.5

26.3

38.0

38.3

-SH

CDCl3

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Thiols Aromatics

The spectra of the thiol containing compounds in this section indicate that the -SH group exerts a very weak deshielding effect on both aliphatic and aromatic position 1 carbons. The aliphatic additivity constants are: HS-

C1=+10.5,

C2 = + 11.4,

C3 = -3.6,

C4 = - 0.2 ppm

The aromatic additivity constants are: HS-

C1= + 2.3,

C2, 6 = + 0.9,

C3, 5 = + 0.5,

C4 = -3.0 ppm

Aromatic Thiols

C-4

C-3,5

C-2,6

C-1

-X

Solvent

125.4

128.9

129.3

130.7

-SH

CDCl3

126.8

128.5

127.9

141.0

-CH2-SH

CDCl3

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The Sadtler Handbook of Proton NMR Spectra

126.9

128.4

126.3

145.7

CDCl3

126.8

129.3

127.7

147.2

CDCl3

4-Substituted Benzenethiols

HS-

C-1

C-2,6

C-3,5

C-4

-X

Solvent

HS-

119.9

132.3

114.7

158.4

-O-CH3

CDCl3

HS-

125.2

131.9

116.1

161.5

-F

CDCl3

HS-

126.7

129.8

129.8

135.3

-CH3

CDCl3

HS-

126.8

129.6

126.0

148.7

HS-

129.0

130.7

129.0

131.6

CDCl3

-Cl

CDCl3

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Sulfones

The wide variety of functional groups containing the –SO2- group displays differing deshielding effects ranging from moderately to strongly deshielding depending upon the type of substituent involved. The aliphatic deshielding observed follows the general sequence shown below for increasing chemical shift effect. -SO2-O-R < -SO2-F < -SO2-OH < -SO2-NH2 < -SO2-CI A similar range of values is noted for the ipso carbon chemical shifts of aromatic - SO2- compounds as shown in the following tables.

Alkyl Chemical Shifts

C-6

C-5

C-4

C-3

C-2

C-1

Compound

Solvent

37.0

CDCl3

37.5

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

43.1

Polysol

44.3

CDCl3

52.6

CDCl3

0.81

44.1

CDCl3

0.81

46.7

CDCl3

0.84

49.1

Polysol

0.92

60.3

CDCl3

13.2

15.9

54.4

CDCl3

14.2

22.6

31.1

24.6

51.9

D2O

R6-

30.5

29.5

25.2

30.1

52.1

D2O

R7-

29.5

29.2

28.4

22.0

53.6

CDCl3

Phenyl Group Chemical Shifts

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The Sadtler Handbook of Carbon NMR Spectra

-SO2-X

C-4

C-3,5

C-2,6

C-1

Solvent

135.9

130.0

128.5

133.3

CDCl3

134.1

128.0

129.5

135.2

CDCl3

133.0

128.3

128.7

137.3

Polysol

133.6

129.3

127.2

140.6

CDCl3

133.2

129.3

127.6

141.6

CDCl3

131.9

128.7

125.7

143.5

Polysol

132.2

129.8

126.3

143.7

H2O

130.6

128.5

125.7

144.1

Polysol

135.5

129.8

126.8

144.2

CDCl3

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Ethers Aliphatics

This section deals with the carbon-13 NMR chemical shifts of aliphatic ethers. The very strong deshielding effect of the oxygen linkage of the ethers is second only to that of fluorine in the chemical shifts observed for adjacent carbon nuclei. The aliphatic additivity constants for several ether groups are:

C1= + 53.8, R10-O

C1 = + 57.0,

C2 = + 6.3, C2 = + 7.3,

C3 = - 6.1, C3 = - 5.6,

C4 = 0.0 ppm C4 = - 0.3 ppm

The tables presented below illustrate representative chemical shifts for a variety of selected spectra of ethers.

Alkyl Chemical Shifts

C-6

C-5

C-4

C-3

C-2

C-1

Compound

49.4

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Solvent CDCl3

The Sadtler Handbook of Carbon NMR Spectra

53.1

CDCl3

54.8

CDCl3

55.1

CDCl3

55.8

CDCl3

57.8

CDCl3

58.8

CDCl3

14.9

63.2

CDCl3

14.6

63.6

CDCl3

15.2

65.7

CDCl3

15.3

66.2

-O-R4

CDCl3

13.9

19.4

31.8

68.3

CDCl3

13.9

19.5

31.5

67.9

CDCl3

14.0

19.7

32.3

70.6

-O-R2

CDCl3

14.0

19.7

32.2

72.9

-O-CH3

CDCl3

14.1

22.8

28.8

29.8

71.1

-O-R5

CDCl3

14.1

22.9

32.0

26.1

30.0

71.1

-O-R6

CDCl3

R5

29.8

29.8

26.5

30.1

71.1

-O-R10

CDCl3

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Ethers Alicyclics

This section deals with the carbon-13 NMR chemical shifts of alicyclic ethers. The very strong deshielding effect of the oxygen linkage of the ethers is second only to that of fluorine in the chemical shifts observed for adjacent carbon nuclei. The aliphatic additivity constants for several ether groups are:

C1= + 53.8, R10-O

C1 = + 57.0,

C2 = + 6.3, C2 = + 7.3,

C3 = - 6.1,

C4 = 0.0 ppm

C3 = - 5.6,

C4 = - 0.3 ppm

Alicyclic Ethers 1,2-Epoxides

C-2

C-1

-R

Solvent

47.7

48.0

- CH3

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

44.4

50.1

CDCl3

44.1

50.8

CDCl3

50.8

52.0

CDCl3

46.5

53.2

CDCl3

Tetrahydrofurans

C-5

C-4

C-3

C-2

-R

68.0

26.0

26.0

68.0

CDCl3

68.2

25.8

28.3

66.5

CDCl3

67.7

26.2

33.5

75.3

67.8

25.2

31.2

75.4

CDCl3

67.6

25.8

32.2

79.4

CDCl3

-CH3

Solvent

CDCl3

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Ethers Aromatics

This section deals with the carbon-13 NMR chemical shifts of aromatic ethers. The very strong deshielding effect of the oxygen linkage of the ethers is second only to that of fluorine in the chemical shifts observed for adjacent carbon nuclei. The aromatic additivity constants for certain ethers are:

R2-O-

C1 = + 29.0,

C2, 6 = - 9.5,

C3, 5 = + 1.3,

C1= + 30.9,

C2, 6 =-13.8,

C3, 5=+1.1,

C4 = - 5.3ppm C4 = - 7.8ppm

Aromatic Chemical Shifts Furan and 2-Substituted Derivatives

C-5

C-4

C-3

C-2

-R

Solvent

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The Sadtler Handbook of Carbon NMR Spectra

142.8

109.7

109.7

142.8

CDCl3

148.0

111.9

122.5

126.5

146.7

112.0

118.1

145.0

CDCl3

146.5

112.1

118.0

145.3

Polysol

145.7

112.2

116.3

149.5

CDCl3

145.9

112.9

116.7

150.6

CDCl3

140.9

110.4

105.6

152.2

142.3

110.3

107.7

154.4

CDCl3

141.5

110.2

104.8

157.4

CDCl3

-C≡N

-CH3

CDCl3

CDCl3

Phenyl Ethers

C-4

C-3

C-2

C-1

Compound

Solvent

122.1

129.4

116.2

157.1

CDCl3

123.1

129.7

118.9

157.4

CDCl3

122.0

129.5

117.2

158.9

CDCl3

120.6

129.5

114.6

159.3

-O-R2

CDCl3

120.7

129.5

114.1

159.9

-O-CH3

CDCl3

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Primary Alcohols Aliphatics and Alicyclics

This section contains the carbon-13 NMR chemical shifts of the primary alcohols. The -OH group produces a strongly deshielded chemical shift for the adjacent carbon of both aliphatic and aromatic compounds. The aliphatic additivity constants are: HO-

C1= + 48.4,

C2 = + 10.1,

C3 = - 6.0,

C4 = 0.0 ppm

The tables that are provided below illustrate typical chemical shifts observed for a variety of selected compounds containing the -OH group.

Alkyl Chemical Shifts

C-6

R7-

C-5

C-4

C-3

C-2

C-1

-OH

Solvent

49.8

-OH

CDCl3

18.2

57.7

-OH

CDCl3

10.3

25.9

64.2

-OH

CDCl3

13.9

19.2

35.0

62.2

-OH

CDCl3

14.1

22.7

28.4

32.6

62.5

-OH

CDCl3

29.9

29.5

26.1

32.9

62.5

-OH

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

Isobutanol

C-3

C-2

C-1

-OH

Solvent

19.1

30.9

69.4

-OH

CDCl3

Alicyclic Alcohols Cyclobutanol

C-3

C-2,4

C-1

-OH

Solvent

12.1

33.4

67.0

-OH

CDCl3

Cyclopentanol

C-3,4

C-2,5

C-1

-OH

Solvent

23.5

35.4

73.6

-OH

CDCl3

Cyclohexanol

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The Sadtler Handbook of Carbon NMR Spectra

C-4

C-3,5

C-2,6

C-1

-OH

Solvent

25.9

24.5

35.5

70.1

-OH

CDCl3

Cycloheptanol

C-4,5

C-3,6

C-2,7

C-1

-OH

Solvent

28.3

22.9

37.6

72.5

-OH

CDCl3

Cyclooctanol

C-5

C-4,6

C-3,7

C-2,8

C-1

-OH

Solvent

25.4

27.6

22.9

34.8

72.0

-OH

CDCl3

Cyclododecanol

C-6,7,8

C-5,9

C-4,10

C-3,11

C-2,12

C-1

-OH

Solvent

23.5

24.4

24.0

21.0

32.5

69.1

-OH

CDCl3

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Primary Alcohols Aromatics

This section contains the carbon-13 NMR chemical shifts of the phenols. The -OH group produces a strongly deshielded chemical shift for the adjacent carbon of both aliphatic and aromatic compounds. The aromatic additivity constants are: HO-

C1= + 26.6,

C2, 6 = -12.8,

C3, 5 =+ 1.4,

C4 = -7.3 ppm

The tables that are provided below illustrate typical chemical shifts observed for a variety of selected compounds containing the -OH group.

Aromatic Alcohols

C-4

C-3,5

C-2,6

C-1

-R

Solvent

128.7

128.5

126.4

136.8

-OH

CDCl3

126.2

130.5

127.9

138.2

-OH

CDCl3

127.2

128.3

126.9

141.0

-OH

CDCl3

127.2

128.2

126.5

143.8

-OH

CDCl3

127.1

128.3

125.5

146.1

-OH

CDCl3

121.1

129.8

115.6

155.0

-OH

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

4-Substituted Phenols

HO-

C-1

HO-

157.1

HO-

C-2,6

C-3,5

C-4

-X

Solvent

118.1

137.7

80.4

-I

Polysol

161.4

116.5

134.0

101.9

-C≡N

Polysol

HO-

153.9

117.2

132.5

113.2

-Br

CDCl3

HO-

161.8

115.4

132.1

121.3

HO-

153.6

116.9

129.7

126.2

-Cl

CDCl3

HO-

155.6

116.3

130.4

127.2

-S-CH 3

Polysol

HO-

162.2

115.4

130.8

129.0

HO-

153.1

115.6

130.2

130.2

HO-

157.2

115.9

127.8

131.7

CDCl3

HO-

160.6

115.4

128.0

133.9

Polysol

HO-

152.3

114.6

121.8

134.5

Polysol

HO-

149.1

115.9

115.7

139.6

HO-

164.5

116.3

126.6

140.9

Polysol

HO-

154.7

114.9

125.9

141.6

Polysol

HO-

151.1

116.6

116.3

157.7

Polysol

Polysol

-CH 3

-NH

-F

2

CDCl3

Polysol

Polysol

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Secondary Alcohols

The -OH group produces a strongly deshielded chemical shift for the adjacent carbon of both aliphatic and aromatic compounds.

5-Nonanol

C-5

C-4

C-3

C-2

C-1

-OH

Solvent

14.1

23.0

28.2

37.4

71.8

-OH

CDCl3

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Tertiary Alcohols

The -OH group produces a strongly deshielded chemical shift for the adjacent carbon of both aliphatic and aromatic compounds.

3-Ethyl-2-Pentanol

C-3

C-2

C-1

-OH

Solvent

7.8

30.6

74.7

-OH

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

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Phenols

This section contains the carbon-13 NMR chemical shifts of the phenols. The -OH group produces a strongly deshielded chemical shift for the adjacent carbon of both aliphatic and aromatic compounds. The aliphatic additivity constants are: HO-

C1= + 48.4,

C2 = + 10.1,

C3 = - 6.0,

C4 = 0.0 ppm

The aromatic additivity constants are: HO-

C1= + 26.6,

C2, 6 = -12.8,

C3, 5 =+ 1.4,

C4 = -7.3 ppm

The tables that are provided below illustrate typical chemical shifts observed for a variety of selected compounds containing the -OH group.

4-Substituted Phenols HO-

C-1

C-2,6

C-3,5

C-4

-X

Solvent

HO-

157.1

118.1

137.7

80.4

-I

Polysol

HO-

161.4

116.5

134.0

101.9

-C≡N

Polysol

HO-

153.9

117.2

132.5

113.2

-Br

CDCl3

HO-

161.8

115.4

132.1

121.3

HO-

153.6

116.9

129.7

126.2

-Cl

CDCl3

HO-

155.6

116.3

130.4

127.2

-S-CH3

Polysol

Polysol

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The Sadtler Handbook of Carbon NMR Spectra

Polysol

HO-

162.2

115.4

130.8

129.0

HO-

153.1

115.6

130.2

130.2

HO-

157.2

115.9

127.8

131.7

CDCl3

HO-

160.6

115.4

128.0

133.9

Polysol

HO-

152.3

114.6

121.8

134.5

Polysol

HO-

149.1

115.9

115.7

139.6

HO-

164.5

116.3

126.6

140.9

Polysol

HO-

154.7

114.9

125.9

141.6

Polysol

HO-

151.1

116.6

116.3

157.7

-CH3

-NH2

-F

CDCl3

Polysol

Polysol

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Ketones Aliphatics

Depending upon their structural environment, the carbonyl (C=O) resonance appears over a chemical shift range of more than 48 ppm (167.8 216.7ppm). As a substituent, the ketone carbonyl group exerts a moderately strong deshielding effect on adjacent C-1 carbons. The aliphatic additivity constants are:

C1= + 29.6,

C1= + 28.7, C

C2 = +1.2,

2 = +1.3,

C3 = - 2.6,

C3 = - 2.8,

C4 = 0.0 ppm

C4 = 0.0 ppm

C1= + 24.5, C2 = +1.6, C3 = - 2.4, C4 = 0.0 ppm A selection of ketone chemical shifts is provided in the following tables.

C-5

C-4

C-3

C-2

C-1

-C(=O)

-R

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Solvent

The Sadtler Handbook of Carbon NMR Spectra

25.5

199.6

CDCl3

26.3

197.4

CDCl3

27.4

197.6

CDCl3

29.3

208.7

CDCl3

8.2

31.7

200.1

CDCl3

7.9

36.8

208.7

13.9

17.9

40.5

199.7

CDCl3

13.8

17.4

42.3

213.5

CDCl3

13.4

17.6

44.8

210.2

13.9

22.5

26.5

38.2

199.7

14.0

22.6

26.3

43.5

208.2

-CH3

CDCl3

14.0

22.7

31.7

23.8

42.7

210.3

-R5

CDCl3

R3-

29.5

29.3

24.1

42.8

210.5

-R7

CDCl3

-CH3

-R3

CDCl3

CDCl3 CDCl3

Branched Alkyl Ketones 2-Methyl-3-Hexanone

C-3

C-2

C-1

-R3

Solvent

18.3

40.8

213.5

-R3

CDCl3

2,6-Dimethyl-4-Heptanone http://www.knowitall.com/handbook/cnmr/ketones/aliphatic/aliphatic.htm（第 2／5 页）2005-10-2 9:21:43

The Sadtler Handbook of Carbon NMR Spectra

C-3

C-2

C-1

-R

Solvent

22.6

24.5

52.4

209.3

CDCl3

-R

Solvent

Alicyclic Ketones Cyclopropyl Ketones

C-2,3

C-1

-C(=O)

11.2

16.8

199.8

CDCl3

11.6

17.0

200.4

CDCl3

10.3

21.1

208.0

-CH3

CDCl3

Cyclobutyl-4-Fluorophenyl Ketone

C-3

C-2,4

C-1

-R

Solvent

18.2

25.1

42.2

199.2

CDCl3

Cyclopentyl Phenyl Ketone

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C-3,5

C-2,4

C-1

-R

Solvent

26.4

30.0

46.4

202.5

CDCl3

Dicyclohexyl Ketone

C-4

C-3,5

C-2,6

C-1

-R

Solvent

26.2

25.9

28.8

49.2

215.7

CDCl3

Cyclooctanone

C-5

C-4,6

C-3,7

C-2,8

-C=O

Solvent

24.9

27.3

25.8

41.9

216.7

CDCl3

Carbonyl Chemical Shifts R-

-C(=O)

-R

Solvent

167.8

-C≡N

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

180.8

-CF3

CDCl3

183.8

CDCl3

194.5

Polysol

C5-

199.2

CDCl3

CH3-

199.6

CDCl3

199.7

-R3

CDCl3

202.5

-C5

CDCl3

CH3-

208.2

-R4

CDCl3

R3-

210.2

-R3

CDCl3

R7-

210.5

-R7

CDCl3

C6-

215.7

-C6

CDCl3

216.7

CDCl3

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Ketones Aromatics

The carbon-13 NMR chemical shifts presented here illustrate typical band intensities of the aromatic ketones. Depending upon their structural environment, the carbonyl (C=O) resonance appears over a chemical shift range of more than 48 ppm (167.8 - 216.7ppm). As a substituent, the ketone carbonyl group exerts a moderately strong deshielding effect on adjacent C-1 carbons. The aromatic additivity constants are: R4-C(=O)-

C1= + 8.9,

C2,6 = -0.4,

C1= + 9.2,

C3, 5 = 0.0,

C2, 6 = +1.4,

C4 = + 4.3 ppm

C3, 5 = 0.0,

C4 = + 3.8 ppm

A selection of ketone chemical shifts is provided in the following tables.

Phenyl Ketones

C-4

C-3,5

C-2,6

C-1

-C(=O)

-R

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Solvent

The Sadtler Handbook of Carbon NMR Spectra

132.6

127.6

126.9

129.4

183.8

-CHCl2

CDCl3

135.8

129.5

130.4

130.4

180.8

-CF3

CDCl3

136.9

129.6

130.3

133.4

167.8

-C≡N

CDCl3

132.7

128.5

129.6

137.0

194.5

132.7

128.5

128.5

137.1 202.5

-C5

CDCl3

132.7

128.5

128.0

137.3 199.7

-R4

CDCl3

132.2

128.2

129.8

137.6 196.1

CDCl3

132.5

128.4

128.4

138.2 189.9

CDCl3

Polysol

Carbonyl Chemical Shifts R-

-C(=O)

-R

Solvent

167.8

-C≡N

CDCl3

180.8

-CF3

CDCl3

183.8

-CHCl2

CDCl3

194.5

Polysol

C5-

199.2

CDCl3

CH3-

199.6

CDCl3

199.7

-R3

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

202.5

-C5

CDCl3

CH3-

208.2

-R4

CDCl3

R3-

210.2

-R3

CDCl3

R7-

210.5

-R7

CDCl3

C6-

215.7

-C6

CDCl3

216.7

CDCl3

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Aldehydes

This section deals with the carbon-13 NMR chemical shifts of the carboxaldehydes. The chemical shifts of adjacent carbon atoms indicate that the carboxaldehyde group exerts a weak to intermediate deshielding effect on both aliphatic and aromatic carbons. The aliphatic additivity constants are:

C1= + 30.0,

C2 = -0.5,

C3 = - 2.5,

C4 = + 0.3 ppm

The phenyl additivity constants are:

C1= + 8.2,

C2, 6 = +1.3,

C3, 5 = + 0.6,

C4 = + 6.0 ppm

The tables presented below contain the chemical shifts for a variety of carboxaldehyde compounds.

N-Alkyl Chemical Shifts

C-6

C-5

C-4

C-3

C-2

C-1

-C(=O)-H

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Solvent

The Sadtler Handbook of Carbon NMR Spectra

13.8

22.5

24.5

43.7

202.0

CDCl3

14.1

22.8

31.9

29.1

22.4

44.1

201.9

CDCl3

R6-

29.8

29.8

29.6

22.3

44.1

201.9

CDCl3

2-Ethylbutyraldehyde

C-3

C-2

C-1

-C(=O)-H

Solvent

11.5

21.7

55.2

204.7

CDCl3

Cyclohexanecarboxaldehyde

C-4

C-3,5

C-2,6

C-1

-C(=O)-H

Solvent

26.1

25.1

26.1

50.0

204.5

CDCl3

Alkenyl Aldehyde Chemical Shifts

C-2

C-1

-C(=O)-H

Solvent

137.8

138.6

194.4

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

C-3

C-2

R3-

C-1

-C(=O)-H

Solvent

158.2 133.3

193.5

CDCl3

152.3 131.1

193.2

CDCl3

148.8 131.8

192.8

CDCl3

R-

C-4

C-3

C-2

C-1

-C(=O)-H

Solvent

R2-

148.4

127.9

152.7

130.3

193.4

CDCl3

R3-

146.7

129.0

152.5

130.2

193.2

CDCl3

R4-

147.0

128.8

152.5

130.2

193.2

CDCl3

Aromatic Aldehydes Benzaldehyde

C-4

C-3,5

C-2,6

C-1

-C(=O)-H

Solvent

134.4

129.0

129.7

136.6

192.0

CDCl3

4-Substituted Benzaldehydes

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The Sadtler Handbook of Carbon NMR Spectra

H-C(=O)

C-1

C-2,6

C-3,5

C-4

-X

Solvent

189.2

124.9

132.0

110.7

152.2

CDCl3

189.5

125.2

131.6

111.0

154.2

CDCl3

190.8

128.7

132.2

116.1

163.5

-OH

Polysol

190.5

130.2

131.9

114.5

164.6

-O-CH3

CDCl3

191.4

134.4

129.6

129.6

145.3

-CH3

CDCl3

191.3

134.9

129.9

127.1

155.9

190.5

134.9

130.8

129.4

140.7

-Cl

CDCl3

190.6

135.2

130.8

132.3

129.4

-Br

CDCl3

191.3

135.2

130.0

127.3

146.6

CDCl3

CDCl3

Aldehydic Carbons H-C(=O)

-X

160.1

161.0

CDCl3

-0-R4

161.6

161.9

CDCl3 CDCl3

-NH-CH2CH3

162.5

163.2

Solvent

CDCl3 CDCl3

-NH-CH3

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

175.9

CDCl3

178.9

CDCl3

189.2

CDCl3

190.6

CDCl3

192.0

CDCl3

193.2

CDCl3

194.4

CDCl3

198.2

CDCl3

201.9

-R11

CDCl3

204.5

-C6

CDCl3

204.7

CDCl3

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Acid Halides

This section contains carbon-13 NMR chemical shifts which are representative for this class of compounds. Although most of the chemical shifts available are of acid chlorides, the chemical shifts observed for several acid bromides indicate that the C(=O)-Br group has a more strongly deshielding effect on adjacent aliphatic groups than does the C(=O)-Cl group. All members of this class react rapidly with traces of moisture to form the corresponding carboxylic acids. Additivity constants for the acid chloride group are given below. The aliphatic additivity constants are:

C1= + 33.1,

C2 = + 2.5,

C3 = - 3.5,

C4 = 0.0 ppm

The aromatic additivity constants are:

C1= + 4.9,

C2, 6 =+ 2.9,

C3, 5 = + 0.8,

C4 = + 7.0 ppm

Alkyl Chemical Shifts

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The Sadtler Handbook of Carbon NMR Spectra

C-1

-X

Solvent

33.7

CDCl3

39.1

CDCl3

R

C-5

C-4

C-3

C-2

C-1

-X

Solvent

R2-

31.8

29.0

28.7

25.4

47.3

CDCl3

R4-

29.4

29.4

28.7

25.4

47.2

CDCl3

R7-

29.6

29.3

28.6

25.3

47.2

CDCl3

Aromatic Chemical Shifts Benzoyl Chloride

C-4

C-3,5

C-2,6

C-1

-C(=O)-Cl

Solvent

135.4

129.2

131.3

133.3

168.0

CDCl3

Phenyl Acetyl Chlorides

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The Sadtler Handbook of Carbon NMR Spectra

C-4

C-3,5

C-2,6

C-1

-R

Solvent

128.1

128.9

129.5

131.4

CDCl3

130.2

128.4

129.3

133.2

CDCl3

128.3

129.1

128.3

136.0

CDCl3

126.7

128.4

128.2

139.4

Polysol

Carbonyl Halide Chemical Shifts X-

C(=O)

-R

Solvent

Br-

165.3

-CH3

CDCl3

Cl-

167.1

CDCl3

Cl-

167.1

CDCl3

Cl-

167.7

CDCl3

Cl-

168.0

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

Cl-

168.9

CDCl3

Cl-

170.3

-CH3

CDCl3

Cl-

173.2

-R12

CDCl3

Cl-

173.4

-R7

CDCl3

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Anhydrides

This section deals with the chemical shifts of the carboxylic anhydrides. As a group, the anhydrides are very reactive and readily decompose to the corresponding carboxylic acid in the presence of the traces of water found in DMSO-d6, polysol and acetone-d6. In general, the carbonyl chemical shift of the anhydride resonates at a higher field than that of the carboxylic acid. The deshielding effect of the anhydride group in relation to adjacent aliphatic carbons is that of a weakly deshielding substituent. The aliphatic additivity constants are:

C1= + 21.1,

C2 = +1.3,

C3 = - 3.6,

C4 = - 0.3 ppm

The anhydride group exerts an intermediate additivity effect on the C1 carbon of phenyl ring carbons as indicated below. The aromatic additivity constants are:

C1= + 6.1,

C2,6 = + 2.1,

C3, 5 = + 0.5,

C4 = + 6.1ppm

The chemical shifts of a selection of anhydride molecules are presented in the tables which follow.

Alkyl Anhydrides

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The Sadtler Handbook of Carbon NMR Spectra

C-5

13.9

C-4

22.5

C-3

31.2

C-2

C-1

-C(=O)-O-C(=O)-R

Solvent

21.9

166.9

CDCl3

8.5

28.8

170.5

CDCl3

24.1

35.3

169.6

CDCl3

C-2

C-1

-C(=O)-O-C(=O)-CH(CH3)2

Solvent

18.3

35.2

172.7

CDCl3

C-3

C-2

C-1

-C(=O)-O-C(=O)-CH(R2)2

Solvent

11.5

24.6

49.9

171.6

CDCl3

Benzoic Anhydride

C-4

C-3,5

C-2,6

C-1

-C(=O)-O-C(=O)-R

Solvent

134.5

128.9

130.5

134.5

162.3

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

Carbonyl Chemical Shifts R-C(=O)-O-C (=O) 161.8

Compound

Solvent CDCl3

166.3

CDCl3

166.9

CDCl3

167.1

CDCl3

169.6

CDCl3

170.5

CDCl3

171.6

CDCl3

171.7

CDCl3

173.3

CDCl3

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Primary Amides

This section concerns itself with the carbon-13 NMR chemical shifts of compounds containing the primary amide group (- C(=O)-NH2). The primary amide group exerts an intermediate deshielding effect on the adjacent aliphatic and aromatic carbons as shown by the additivity constants provided below. The aliphatic additivity constants are:

C1= + 21.6,

C2 = + 3.1,

C3 = - 2.4,

C4 = 0.0 ppm

The phenyl additivity constants are:

C1= + 5.6,

C2,6 = -0.7,

C3, 5 = - 0.2,

C4 = + 2.9 ppm

As indicated in the following chemical shift tables, the primary amide compounds are not readily soluble in CDCI3 and usually require the use of DMSO-d6 or DMSO-d6/CDCI3 mixture (polysol) in order to obtain high quality carbon-13 spectra.

Alkyl Chemical Shifts

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The Sadtler Handbook of Carbon NMR Spectra

C-6

R3-

C-5

29.1

C-4

C-3

C-2

-C(=O)-NH2

C-1

Solvent

22.3

Polysol

9.7

29.0

CDCl3

13.7

22.3

27.7

35.8

CDCl3

29.1

29.1

25.4

35.5

Polysol

Crotonamide

C-4

C-3

C-2

C-1

17.3

138.2

126.1

167.2

-C(=O)-NH2

Solvent Polysol

2-Furamide

C-5

C-4

C-3

C-2

-C(=O)-NH2

Solvent

144.6

111.7

113.9

148.0

160.1

Polysol

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Phenyl Amides

C-4

C-3,5

C-2,6

C-1

-X

Solvent

126.3

129.0

128.2

136,2

Polysol

131.3

128.2

127.7

134.0

Polysol

Carbonyl Chemical Shifts

H2N-C(=O)

-R

Solvent

160.1

Polysol

167.2

Polysol

172.6

-CH3

Polysol

175.3

-R8

Polysol

176.5

-R6

CDCl3

177.5

-R2

CDCl3

181.3

Polysol

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Secondary Amides

The data contained in this section deal with the N-substituted secondary amides (R-C(=O)-NH-R'). Due to the presence of the N-substituent, the range of chemical shifts is larger than that observed for the primary amides. The additivity effect of either side of the -C(=O)-NH- group is that of an intermediate deshielding group as they also are with the adjacent carbons of phenyl groups. The alkyl additivity constants are:

C1= + 22.7,

C2 = + 3.1,

C3 = - 2.6,

C4 = 0.0 ppm

C1= + 25.8,

C2 = + 6.6,

C3 = - 4.9,

C4 = 0.0 ppm

The phenyl additivity constants are:

C1=+10.8, C2,6 = -8.7, C3, 5 =+ 0.1, C4 = -5.1ppm

C1= + 6.2, C2, 6 =-1.2, C3, 5 =-0.1, C4 = + 2.8ppm The tables provided below display the chemical shifts for a selection of secondary amide compounds.

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Alkyl Chemical Shifts

C-6

C-5

C-4

C-3

C-1

-NH-C(=O)-R

Solvent

22.8

CDCl3

10.2

29.5

CDCl3

9.9

30.4

CDCl3

13.7

19.1

39.1

Polysol

25.9

36.8

CDCl3

R12-

29.7

29.5

29.5

C-4

C-3

C-2

CH3

11.5

C-2

-NH-C(=O)-R

Solvent

26.3

CDCl3

26.7

CDCl3

14.6

34.4

CDCl3

23.0

41.4

CDCl3

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13.6

20.3

31.6

39.6

CDCl3

Aromatic Chemical Shifts N-Substituted Benzamides

C-4

C-3,5

C-2,6

C-1

-C(=O)-NH-R

Solvent

131.2

128.3

127.2

134.6

CDCl3

131.2

128.2

127.7

135.3

Polysol

130.9

128.3

126.8

136.0

CDCl3

N-Phenyl Amides

C-4

C-3,5

C-2,6

125.1

128.9

118.7

C-1

-NH-C(=O)-R

Solvent CDCl3

137.0

(syn) 124.7

129.6

120.3

CDCl3

137.2

(anti) 124.2

128.8

120.5

138.4

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

123.3

128.5

119.7

139.2

Polysol

123.6

128.4

120.6

139.3

Polysol

Carbonyl Chemical Shifts R-

C(=O)-NH

-R

Solvent

H-

160.1

CDCl3

165.8

Polysol

168.8

-CH3

CDCl3

CH3-

171.0

-R2

CDCl3

CH3-

171.2

-R4

CDCl3

R2-

173.3

R17-

174.0

CDCl3

-CH3

CDCl3

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Tertiary Amides

With a wider range of possible substituent combinations, the chemical shift ranges observed for the tertiary amides are generally larger than those of the secondary amides. A selection of additivity constants for aliphatic and aromatic tertiary amides is provided below. The aliphatic additivity constants are:

C1- + 19.1,

C2 = + 2.9,

C3 = -2.4,

C4 = + 0.2 ppm

The aromatic additivity constants are:

C1= + 8.1,

(syn)

C1= + 11.4,

C2, 6 =-1.4,

C2,6 = - 2.3,

C3,5 = - 0.3,

C4 = + 0.9 ppm

C3,5 = + 1.2,

C4 = -1.6ppm

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(anti)

C1=+13.4,

C2,6 = - 3.3,

C3,5 = + 0.7

C4 = - 1.4ppm

C1= + 15.0,

C2,6 = - 0 2,

C3,5 = + 1 2

C4 = -0.7ppm

The following tables contain the chemical shifts from a selection of aliphatic and aromatic compounds.

Alkyl Chemical Shifts

C-6

R4-

C-5

29.7

C-4

29.7

C-3

C-2

C-1

-C(=O)-N(R,R)

Solvent

21.4

CDCl3

21.4

CDCl3

22.6

CDCl3

9.6

26.2

CDCl3

14.0

18.7

35.2

CDCl3

29.7

25.7

33.2

CDCl3

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Higher Field (syn) Isomers C-4

13.8

C-3

C-2

C-1

-N(R)-C(=O)-R’

Solvent

31.1

CDCl3

34.8

CDCl3

35.2

CDCl3

13.2 40.2

CDCl3

13.5 40.2

CDCl3

11.2

21.0 47.4

CDCl3

11.4

21.2 47.6

CDCl3

19.8

29.7 41.9

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

Lower Field (anti) Isomers C-4

13.8

C-3

C-2

C-1

-N(R)-C(=O)-R’

Solvent

36.1

CDCl3

37.9

CDCl3

38.9

CDCl3

13.5 41.0

CDCl3

14.4 42.0

CDCl3

13.5 42.5

CDCl3

11.4

22.6 49.8

CDCl3

11.2

22.2 50.6

CDCl3

20.3

31.1 47.1

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

Phenyl Chemical Shifts

C-4

C-3,5

C-2,6

-C(=O)-N(R)2

C-1

Solvent

130.1

128.4 127.6

135.4

CDCl3

129.3

128.1 127.0

136.5

CDCl3

129.1

128.3 126.7

136.6

CDCl3

C-4

C-3,5

126.8

129.6

127.0

129.1

C-2,6

C-1

Compound

Solvent CDCl3

126.1 139.8

(syn) 125.1

CDCl3

141.8

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The Sadtler Handbook of Carbon NMR Spectra

127.7

129.6

128.2

143.4

CDCl3

Carbonyl Chemical Shifts R-

C(=O)

-N(R,R’)

Solvent

H-

161.6

CDCl3

H-

162.5

CDCl3

168.3

CDCl3

CH3-

169.4

CDCl3

CH3-

170.1

CDCl3

171.0

CDCl3

R9-

172.4

CDCl3

R2-

172.5

CDCl3

R3-

172.8

CDCl3

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Carboxylic Acids Aliphatics

The carbon-13NMR chemical shifts covered in this section contain the carboxylic acid group (- C(=O)- OH) as a common denominator. Because many of these compounds present solubility problems, a significant difference in chemical shifts of the carboxylic acid group is observed depending upon the solvent employed in preparing the spectrogram. The chemical shift effect of the carboxylic acid group is that of an intermediate deshielding substituent in its effect on aliphatic groups and a weakly deshielding moiety in its effect on adjacent aromatic carbons. The aliphatic additivity constants are:

C1= + 20.2,

C2 = + 2.1,

C3 = - 2.8,

C4 = 0.0 ppm

The aromatic additivity constants are:

C1=+1.1,

C2, 6 = + 1.9,

C3, 5 = + 0.1 C

4 = + 5.4 ppm

The overall chemical shift range for the carbonyl resonance is more than 29ppm (156.5- 185.8ppm) as shown in the chemical shift tables given below.

Alkyl Chemical Shifts

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The Sadtler Handbook of Carbon NMR Spectra

C-6

C-5

C-4

C-3

C-2

C-1

-C(=O)-OH

Solvent

20.7

177.7

CDCl3

8.9

27.7

181.2

CDCl3

13.7

18.6

36.3

180.5

CDCl3

13.7

22.5

27.1

34.0

180.5

CDCl3

13.9

22.5

31.5

24.7

34.3

180.5

CDCl3

14.0

22.7

31.7

28.9

24.9

34.3

180.8

CDCl3

R3-

29.5

29.5

29.3

24.9

34.3

180.6

CDCl3

R9-

29.7

29.7

29.4

25.0

34.2

175.8

Polysol

R11-

29.7

29.7

29.3

25.0

34.3

176.3

Polysol

Alicyclic Chemical Shifts Cyclopropanecarboxylic Acid

C-2,3

C-1

-C(=O)-OH

Solvent

9.2

13.1

181.9

CDCl3

Cyclobutanecarboxylic Acid

C-3

C-2,4

C-1

-C(=O)-OH

Solvent

18.6

25.4

38.4

181.9

CDCl3

Cyclopentanecarboxylic Acid

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The Sadtler Handbook of Carbon NMR Spectra

C-3,4

C-2,5

C-1

-C(=O)-OH

Solvent

26.0

30.1

43.9

183.5

CDCl3

Cyclohexanecarboxylic Acid

C-4

C-3,5

C-2,6

C-1

-C(=O)-OH

Solvent

25.9

25.5

29.0

43.1

183.0

CDCl3

C-4

C-3,5

C-2,6

C-1

-CH 2

26.3

26.2

33.2

34.9

42.0

-C(=O)-OH 179.7

Solvent CDCl3

Cycloheptanecarboxylic Acid

C-4,5

C-3,6

C-2,7

C-1

-C(=O)-OH

Solvent

28.5

26.5

30.7

45.0

183.8

CDCl3

Carbonyl Chemical Shifts HO-C(=O)156.5 166.2

-R

Solvent

-C≡C-H

CDCl3 Polysol

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The Sadtler Handbook of Carbon NMR Spectra

166.9

Polysol

167.1

Polysol

168.2

Polysol

169.1

Polysol

170.4

D2O (HCl)

172.3

CDCl3

172.4

CDCl3

(trans) 172.7

CDCl3

175.5

D2O

175.8

-R15

Polysol

178.4

CDCl3

179.7

CDCl3

180.6

-R8

CDCl3

181.2

CDCl3

183.0

CDCl3

183.8

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

185.8

CDCl3

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Carboxylic Acids Aromatics

The carbon-13NMR chemical shifts covered in this section contain the carboxylic acid group (- C(=O)- OH) as a common denominator. Because many of these compounds present solubility problems, a significant difference in chemical shifts of the carboxylic acid group is observed depending upon the solvent employed in preparing the spectrogram. The chemical shift effect of the carboxylic acid group is that of an intermediate deshielding substituent in its effect on aliphatic groups and a weakly deshielding moiety in its effect on adjacent aromatic carbons. The aliphatic additivity constants are:

C1= + 20.2,

C2 = + 2.1,

C3 = - 2.8,

C4 = 0.0 ppm

The aromatic additivity constants are:

C1=+1.1,

C2, 6 = + 1.9,

C3, 5 = + 0.1

C4 = + 5.4 ppm

The overall chemical shift range for the carbonyl resonance is more than 29ppm (156.5- 185.8ppm) as shown in the chemical shift tables given below.

Phenyl Chemical Shifts

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C-4

C-3,5

C-2,6

C-1

-X

Solvent

133.8

128.5

130.3

129.5

CDCl3

135.6

130.8

129.0

131.8

CDCl3

127.3

129.4

128.6

133.3

CDCl3

127.4

128.7

127.7

139.9

CDCl3

126.5

130.1

127.5

143.3

Polysol

4-Substituted Benzoic Acids

HO-C(=O)-

C-1

168.2

C-2,6

C-3,6

C-4

131.1

110.6

153.1

132.1

115.4

161.8

-X

Solvent Polysol

117.4 169.1

121.3

-OH

Polysol

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167.4 167.1 166.8 166.9

123.3 127.6 129.8 130.2

171.4

131.5

113.5

162.9

-O-CH3

Polysol

132.3

115.4

165.5

-F

Polysol

131.1

128.5

138.3

-Cl

Polysol

131.2

131.5

127.1

-Br

Polysol

129.3

129.3

134.6

130.0

132.2

115.5

130.1

129.3

139.0

Polysol

134.6 166.2

135.1

166.8

-C≡N

Polysol Polysol

136.0

Carbonyl Chemical Shifts HO-C(=O)156.5

-R

Solvent

-C≡C-H

CDCl3

166.2

Polysol

166.9

Polysol

167.1

Polysol

168.2

Polysol

169.1

Polysol

170.4

D2O (HCl)

172.3

CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

172.4

CDCl3

(trans) 172.7

CDCl3

175.5

D2O

175.8

-R15

Polysol

178.4

CDCl3

179.7

CDCl3

180.6

-R8

CDCl3

181.2

CDCl3

183.0

CDCl3

183.8

CDCl3

185.8

CDCl3

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Esters Aliphatics

The carbon-13 chemical shifts contained in this section display the chemical shifts and spectrum patterns produced by the carboxylic acid ester functional group (R-C(=O)- O-R'). The carbonyl side of the bond exerts a weak to intermediate deshielding effect on the adjacent (C1) carbons of both aliphatic and aromatic compounds. The oxygen side of the bond, on the other hand, has a strongly deshielding effect on these carbons. The aliphatic additivity constants are:

C1= + 20.1,

C1= + 50.5,

C2 = + 2.4,

C3 = - 2.6,

C2 = + 6.0,

C3 = - 6.0,

C4 = 0.0 ppm

C4 = 0.0 ppm

The aromatic additivity constants are:

C1= + 2.1,

C2, 6 = +1.3,

C1 = + 22.7,

C3, 5 = + 0.1,

C2, 6 = - 6.7,

C4 = + 4.5 ppm

C3, 5 = + 1.0,

C4 = - 2.8 ppm

The chemical shift tables presented below contain the shifts for a selected group of carboxylic acid esters.

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The Sadtler Handbook of Carbon NMR Spectra

Alkyl Chemical Shifts

C-5

R5-

C-4

C-3

C-2

C-1

-C(=O)

-O-R

Solvent

19.4

170.6

-R4

CDCl3

20.4

167.7

CDCl3

20.7

169.1

CDCl3

22.3

170.0

CDCl3

8.8

27.3

171.3

CDCl3

9.3

27.6

174.6

9.0

27.7

172.6

CDCl3

9.0

27.8

173.1

CDCl3

13.6

18.4

35.9

170.5

CDCl3

13.7

18.6

36.1

173.9

13.7

18.7

36.6

172.7

13.7

18.8

36.7

172.5

13.8

22.5

27.3

34.2

173.5

13.7

22.5

27.2

34.4

172.6

29.4

29.3

24.8

34.0

170.4

-CH3

-CH3

CDCl3

CDCl3 CDCl3

-C6

CDCl3 CDCl3

-3-Cholesterol

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CDCl3 CDCl3

The Sadtler Handbook of Carbon NMR Spectra

R15-

29.5

29.5

25.2

34.2

174.1

R9-

29.5

29.3

25.2

34.7

172.8

C-5

C-4

C-3

C-1

-O-C(=O)

-R

Solvent

51.2

173.8

-R5

CDCl3

51.5

166.5

CDCl3

51.6

171.6

CDCl3

52.0

165.9

CDCl3

14.4

59.9

175.7

-C6

CDCl3

14.3

60.4

170.7

-CH3

CDCl3

14.3

62.0

164.5

14.4

63.7

155.5

-O-R2

CDCl3

14.0

68.6

150.5

-Cl

CDCl3

10.4

22.4

65.6

161.2

-H

CDCl3

10.5

22.2

66.4

166.4

CDCl3

10.4

22.4

66.9

154.2

CDCl3

13.7

19.4

31.0

63.7

161.0

13.8

19.5

31.1

64.7

166.3

13.7

19.1

30.7

72.4

150.6

-Cl

CDCl3

29.5

26.1

28.8

64.6

170.8

-CH3

CDCl3

R14-

C-2

-CH3

CDCl3 CDCl3

CDCl3

-H

CDCl3 CDCl3

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The Sadtler Handbook of Carbon NMR Spectra

Cyclohexyl Ester Chemical Shifts

C-4

C-3,5

C-2,6

C-1

-C(=O)-O

-R

Solvent

26.0

25.7

29.2

43.2

176.2

-CH3

CDCl3

26.1

25.7

29.2

43.5

175.3

CDCl3

26.1

25.8

29.3

43.5

175.7

CDCl3

C-4

C-3,5

C-2,6

C-1

-O-C(=O)

-R

Solvent

25.8

24.0

32.0

72.7

172.5

-R3

CDCl3

25.6

23.7

31.7

72.3

167.6

25.7

23.9

31.9

72.5

170.1

CDCl3

-CH3

Carbonyl Chemical Shifts R-

-C(=O)-O

Cl-

149.3

Cl-

150.6

-R

Solvent CDCl3

-R4

CDCl3

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CDCl3

The Sadtler Handbook of Carbon NMR Spectra

H-C≡C-

R6-0-

152.0

CDCl3

152.8

CDCl3

154.2

-R3

CDCl3

155.6

-R6

CDCl3

156.5

CDCl3

CH3-0-

157.1

-CH3

CDCl3

NH2-

157.6

-R12

CDCl3

NH2-

158.4

-CH3

Polysol

H-

161.2

H-

161.9

CDCl3 -CH3

CDCl3

165.9

CDCl3

166.3

CDCl3

166.4

-R3

CDCl3

166.5

-CH3

CDCl3

167.0

-CH3

Polysol

CH3-

167.7

CDCl3

CH3-

170.0

CDCl3

C6-

170.4

-R6

CDCl3

172.5

-R3

CDCl3

http://www.knowitall.com/handbook/cnmr/esters/aliphatic/aliphatic.htm（第 5／6 页）2005-10-2 9:26:31

The Sadtler Handbook of Carbon NMR Spectra

R3-

172.7

CDCl3

R2-

173.1

CDCl3

R5-

173.8

C4-

175.4

CDCl3

C6-

175.7

CDCl3

178.6

-CH3

-CH3

CDCl3

CDCl3

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

http://www.knowitall.com/handbook/cnmr/esters/aliphatic/aliphatic.htm（第 6／6 页）2005-10-2 9:26:31

The Sadtler Handbook of Carbon NMR Spectra

Go to: home • ir • proton nmr • carbon nmr • mass spec

Esters Olefinics

The carbon-13 chemical shifts contained in this section display the chemical shifts and spectrum patterns produced by the carboxylic acid ester functional group (R-C(=O)- O-R'). The carbonyl side of the bond exerts a weak to intermediate deshielding effect on the adjacent (C1) carbons of both aliphatic and aromatic compounds. The oxygen side of the bond, on the other hand, has a strongly deshielding effect on these carbons. The aliphatic additivity constants are:

C1= + 20.1, C2 = + 2.4, C3 = - 2.6, C4 = 0.0 ppm

C1= + 50.5, C2 = + 6.0, C3 = - 6.0, C4 = 0.0 ppm The aromatic additivity constants are:

C1= + 2.1, C2, 6 = +1.3, C3, 5 = + 0.1, C4 = + 4.5 ppm

- C1 = + 22.7, C2, 6 = - 6.7, C3, 5 = + 1.0, C4 = - 2.8 ppm The chemical shift tables presented below contain the shifts for a selected group of carboxylic acid esters.

http://www.knowitall.com/handbook/cnmr/esters/olefinic_esters_aliphatic_acids/olefinic_esters_aliphatic_acids.htm（第 1／4 页）2005-10-2 9:26:45

The Sadtler Handbook of Carbon NMR Spectra

Acrylate Chemical Shifts

CH2-

CH

-C(=O)-O

-R

Solvent

130.4

128.8

166.5

-CH3

CDCl3

130.7

128.2

165.9

129.8

129.2

165.9

CDCl3

-R4

CDCl3

Vinyl Ester Chemical Shifts

CH2-

CH

-C(=O)-O

-R

Solvent

97.0

141.5

170.4

-R9

CDCl3

97.0

141.7

171.3

97.2

141.6

167.7

CDCl3 -CH3

CDCl3

Carbonyl Chemical Shifts R-

-C(=O)-O

Cl-

149.3

Cl-

150.6

-R

Solvent CDCl3

-R4

CDCl3

http://www.knowitall.com/handbook/cnmr/esters/olefinic_esters_aliphatic_acids/olefinic_esters_aliphatic_acids.htm（第 2／4 页）2005-10-2 9:26:45

The Sadtler Handbook of Carbon NMR Spectra

H-C≡C-

R6-0-

152.0

CDCl3

152.8

CDCl3

154.2

-R3

CDCl3

155.6

-R6

CDCl3

156.5

CDCl3

CH3-0-

157.1

-CH3

CDCl3

NH2-

157.6

-R12

CDCl3

NH2-

158.4

-CH3

Polysol

H-

161.2

H-

161.9

CDCl3 -CH3

CDCl3

165.9

CDCl3

166.3

CDCl3

166.4

-R3

CDCl3

166.5

-CH3

CDCl3

167.0

-CH3

Polysol

CH3-

167.7

CDCl3

CH3-

170.0

CDCl3

C6-

170.4

-R6

CDCl3

172.5

-R3

CDCl3

http://www.knowitall.com/handbook/cnmr/esters/olefinic_esters_aliphatic_acids/olefinic_esters_aliphatic_acids.htm（第 3／4 页）2005-10-2 9:26:45

The Sadtler Handbook of Carbon NMR Spectra

R3-

172.7

CDCl3

R2-

173.1

CDCl3

R5-

173.8

C4-

175.4

CDCl3

C6-

175.7

CDCl3

178.6

-CH3

-CH3

CDCl3

CDCl3

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

http://www.knowitall.com/handbook/cnmr/esters/olefinic_esters_aliphatic_acids/olefinic_esters_aliphatic_acids.htm（第 4／4 页）2005-10-2 9:26:45

The Sadtler Handbook of Carbon NMR Spectra

Go to: home • ir • proton nmr • carbon nmr • mass spec

Esters Aromatics

The carbon-13 chemical shifts contained in this section display the chemical shifts and spectrum patterns produced by the carboxylic acid ester functional group (R-C(=O)- O-R'). The carbonyl side of the bond exerts a weak to intermediate deshielding effect on the adjacent (C1) carbons of both aliphatic and aromatic compounds. The oxygen side of the bond, on the other hand, has a strongly deshielding effect on these carbons. The aliphatic additivity constants are:

C1= + 20.1, C2 = + 2.4, C3 = - 2.6, C4 = 0.0 ppm

C1= + 50.5, C2 = + 6.0, C3 = - 6.0, C4 = 0.0 ppm The aromatic additivity constants are:

C1= + 2.1, C2, 6 = +1.3, C3, 5 = + 0.1, C4 = + 4.5 ppm

C1 = + 22.7, C2, 6 = - 6.7, C3, 5 = + 1.0, C4 = - 2.8 ppm The chemical shift tables presented below contain the shifts for a selected group of carboxylic acid esters.

http://www.knowitall.com/handbook/cnmr/esters/aromatic_aliphatic/aromatic_aliphatic.htm（第 1／4 页）2005-10-2 9:27:00

The Sadtler Handbook of Carbon NMR Spectra

Aromatic Chemical Shifts Benzyl Compounds

C-4

C-3,5

C-2,6

C-1

-R

Solvent

127.1

129.4

128.6

134.4

CDCl3

128.5

128.5

128.2

136.0

CDCl3

127.8

128.5

126.1

142.2

CDCl3

C-2,6

C-1

Benzoates

C-4

C-3,5

-C(=O)-O

-R

Solvent

133.4

128.5

129.7

130.0

164.8

CDCl3

132.8

128.4

129.6

130.9

166.3

-CH2CH3

CDCl3

132.7

128.3

129.6

130.9

166.4

-R3

CDCl3

Phenyl Esters

C-4

C-3,5

C-2,6

C-1

-O-C (=O)

-R

Solvent

http://www.knowitall.com/handbook/cnmr/esters/aromatic_aliphatic/aromatic_aliphatic.htm（第 2／4 页）2005-10-2 9:27:00

The Sadtler Handbook of Carbon NMR Spectra

125.6

129.4

121.7

151.1

169.2

- CH3

CDCl3

125.7

129.4

121.7

151.1

164.8

124.9

129.0

121.8

151.2

155.3

-NH2

Polysol

127.2

129.9

120.5

151.8

149.

-Cl

CDCl3

CDCl3

Carbonyl Chemical Shifts R-

-C(=O)-O

Cl-

149.3

Cl-

150.6

H-C≡C-

R6-0-

-R

Solvent CDCl3

-R4

CDCl3

152.0

CDCl3

152.8

CDCl3

154.2

-R3

CDCl3

155.6

-R6

CDCl3

156.5

CDCl3

CH3-0-

157.1

-CH3

CDCl3

NH2-

157.6

-R12

CDCl3

NH2-

158.4

-CH3

Polysol

H-

161.2

H-

161.9

CDCl3 -CH3

CDCl3

165.9

CDCl3

166.3

CDCl3

http://www.knowitall.com/handbook/cnmr/esters/aromatic_aliphatic/aromatic_aliphatic.htm（第 3／4 页）2005-10-2 9:27:00

The Sadtler Handbook of Carbon NMR Spectra

166.4

-R3

CDCl3

166.5

-CH3

CDCl3

167.0

-CH3

Polysol

CH3-

167.7

CDCl3

CH3-

170.0

CDCl3

170.4

-R6

CDCl3

C6-

172.5

-R3

CDCl3

R3-

172.7

CDCl3

R2-

173.1

CDCl3

R5-

173.8

C4-

175.4

CDCl3

C6-

175.7

CDCl3

178.6

-CH3

-CH3

CDCl3

CDCl3

Published by Bio-Rad Laboratories, Inc., Informatics Division. © 1978-2004 Bio-Rad Laboratories, Inc. All Rights Reserved.

http://www.knowitall.com/handbook/cnmr/esters/aromatic_aliphatic/aromatic_aliphatic.htm（第 4／4 页）2005-10-2 9:27:00