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Infrared Absorption Frequencies

Infrared Absorption Frequencies

Numbers separated by dashes are ranges; when two numbers are separated by a comma, both absorptions are expected. Individual numbers not components of a range should be considered 5 cm-1. Intensity of absorptions (relative height of peak) is keyed by letter: s = strong; m = medium; w = weak; v = very; br = broad. Compound Class Structure n , cm -1 2850-3000 Alkanes RCH2CH3 1450-1470 1370-1380 720-725 3040-3140 Alkenes RCH=CH2 1655 910, 990 3080-3140 R2C=CH2 1650 890 3020 Z- RCH=CHR 1660 675-725 (a) 3-ring (b) 4-ring (c) 5-ring (d) 6-ring (e) 7-ring
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Intensity s s s m m m s s m s w w m w w w w w

Assignment CH stretch CH2 and CH3 bending modes =C-H stretch C=C stretch =CH out of plane =C-H stretch C=C stretch =CH out of plane =C-H stretch C=C stretch =CH out of plane C=C stretch " " " "
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1641 1566 1611 1649 1651

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Infrared Absorption Frequencies

(f) 8-ring

1653 3020

w w w s w w s vw to missing s m s vw to missing s s s out of range varies s varies s s s s s

" =C-H stretch C=C stretch

=CH out of plane

E- RCH=CHR

1675 970 3020

=C-H stretch C=C stretch =CH out of plane C=C stretch CH stretch CC stretch C-H bend C C stretch C-F stretch C-Cl stretch C-Br stretch C-I stretch OH stretch C-O stretch OH stretch C-O stretch OH stretch C-O stretch C=O stretch C=O stretch
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R2C=CHR

1670 790-840

R2C=CR2

1670 3300

Alkynes

RC CH

2100-2140 600-700

RC CR Alkyl Halides R-F R-Cl R-Br R-I Alcohols RCH2OH

2190-2260 1000-1350 750-850 500-680 200-500 3400-3600 1050 3400-3600 1100 3400-3600 1070-1150 1725 1685

R2CHOH R3COH Ethers Aldehydes R-O-R RCHO C=CCHO

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Infrared Absorption Frequencies

ArCHO All aldehydes Ketones R2CO (a) 4-ring (b) 5-ring (c) 6-ring C=CCOR ArCOR

1700 2720, 2820 (both) 1715 1780 1745 (doublet) 1715 1675 1690 3400

s m s " " " m s s s s (broad) s s s s (broad) s

>m "

C=O stretch CHO out of plane C=O stretch " " " " " monomer OH monomer C=O dimer OH dimer C=O monomer OH monomer C=O dimer OH dimer C=O C-O stretch " C=O stretch " " " " NH stretch (free)
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Carboxylic Acids

RCO2H

1760 2800-3400 1710 3400 1720

C=CCO2H

2800-3400 1690

RCO2Esters RCO2R' (a) 5-ring (b) 6-ring C=CCO2R ArCO2R

1550-1610 1400 1735 1770 1735 1720 1720 3500

s s s s s m

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Infrared Absorption Frequencies

1690 Amides RCONH2 3400 1650 1600-1640 3440 1680 RCONHR 3330 1650 1530-1550 (a) 4-ring (b) 5-ring (c) 6-ring RCONR2 Anhydrides Acid Chloride RCO2COR RCOCl 1745 1700 1640 1650 1760, 1820 (both) 1800 3400, 3500 (both) Amines RNH2 1560-1640 1030-1230 R2NH 3310-3350 1030-1230 3450 1250-1360 730-770 690-710

s m s s m s m s m s " " m s s w s m w m w s m m

C=O stretch (free) NH str. (H-bond) C=O str. (H-bond) NH out of plane NH stretch (free) C=O stretch (free) NH str. (H-bond) C=O str. (H-bond) NH out of plane C=O stretch " " C=O stretch C=O stretch; symm., unsymm. C=O stretch NH stretch NH2 in plane bend C-N stretch NH stretch C-N stretch NH stretch Ar-N stretch CH out of plane bending
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Ar2NH

Benzenes

monosubst.

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Infrared Absorption Frequencies

ortho-disub. meta-disub. para-disub. 1,2,3-trisub.

735-770 750-810 690-710 810-840 760-780 705-745 810-865 675-730 805-825 870-885 800-810 855-870 840-850 870 References

m m m m m m m m m m m m m w

" " " "

1,3,5-trisub.

"

1,2,4-trisub. 1,2,3,4tetrasub. 1,2,4,5tetrasub. 1,2,3,5tetrasub. 1,2,3,4,5pentasub.

" " " " "

1. Bellamy, L. J., "The Infrared Spectra of Complex Molecules", 2nd edition, John Wiley & Sons, New York, 1961. 2. Nakanishi, K. "Infrared Absorption spectroscopy - Practical", Holden-Day, Inc., San Francisco, 1962.
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