Characteristic IR Absorption Frequencies of Organic Functional Groups

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Characteristic IR Absorption Frequencies of Organic Functional Groups Functional Group Type of Vibration Characteristic Absorptions (cm- 1) Intensity Alcohol O-H (stretch, H-bonded) 3200-3600 strong, broad O-H (stretch, free) 3500-3700 strong, sharp C-O (stretch) 1050-1150 strong Alkane C-H stretch 2850-3000 strong -C-H bending 1350-1480 variable Alkene =C-H stretch 3010-3100 medium =C-H bending 675-1000 strong C=C stretch 1620-1680 variable Alkyl Halide C-F stretch 1000-1400 strong C-Cl stretch 600-800 strong C-Br stretch 500-600 strong C-I stretch 500 strong Alkyne C-H stretch 3300 strong,sharp stretch 2100-2260 variable, not present in

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Transcript of Characteristic IR Absorption Frequencies of Organic Functional Groups

Characteristic IR Absorption Frequencies of Organic Functional Groups

Functional GroupType of VibrationCharacteristic Absorptions (cm-1)Intensity

Alcohol

O-H(stretch, H-bonded)3200-3600strong, broad

O-H(stretch, free)3500-3700strong, sharp

C-O(stretch)1050-1150strong

Alkane

C-Hstretch2850-3000strong

-C-Hbending1350-1480variable

Alkene

=C-Hstretch3010-3100medium

=C-Hbending675-1000strong

C=Cstretch1620-1680variable

Alkyl Halide

C-Fstretch1000-1400strong

C-Clstretch600-800strong

C-Brstretch500-600strong

C-Istretch500strong

Alkyne

C-Hstretch3300strong,sharp

stretch2100-2260variable, not present in symmetrical alkynes

Amine

N-Hstretch3300-3500medium (primary amines have two bands; secondary have one band, often very weak)

C-Nstretch1080-1360medium-weak

N-Hbending1600medium

Aromatic

C-Hstretch3000-3100medium

C=Cstretch1400-1600medium-weak, multiple bands

Analysis of C-H out-of-plane bending can often distinguish substitution patterns

CarbonylDetailed Information on Carbonyl IR

C=Ostretch1670-1820strong

(conjugation moves absorptions to lower wave numbers)

Ether

C-Ostretch1000-1300 (1070-1150)strong

Nitrile

CNstretch2210-2260medium

Nitro

N-Ostretch1515-1560 & 1345-1385strong, two bands

IR Absorption Frequencies of Functional Groups Containing a Carbonyl (C=O)

Functional GroupType of VibrationCharacteristic Absorptions (cm-1)Intensity

Carbonyl

C=Ostretch1670-1820strong

(conjugation moves absorptions to lower wave numbers)

Acid

C=Ostretch1700-1725strong

O-Hstretch2500-3300strong, very broad

C-Ostretch1210-1320strong

Aldehyde

C=Ostretch1740-1720strong

=C-Hstretch2820-2850 & 2720-2750medium, two peaks

Amide

C=Ostretch1640-1690strong

N-Hstretch3100-3500unsubstituted have two bands

N-Hbending1550-1640

Anhydride

C=Ostretch1800-1830 & 1740-1775two bands

Ester

C=Ostretch1735-1750strong

C-Ostretch1000-1300two bands or more

Ketone

acyclicstretch1705-1725strong

cyclicstretch3-membered - 18504-membered - 17805-membered - 17456-membered - 17157-membered - 1705strong

a,b-unsaturatedstretch1665-1685strong

aryl ketonestretch1680-1700strong

A good general reference for more detailed information on interpretation of infrared spectra (as well as other spectroscopic techniques) is Silverstein, R.M.; Bassler, G.C.; and Morrill, T.C.Spectrometric Identification of Organic Compounds.4th ed. New York: John Wiley and Sons, 1981. QD272.S6 S55A more complete listing of functional group absorption frequencies ma be found in: Nakanishi, KojiInfrared Absorption Spectroscopy. QD95.N383


Graphical Displays of Data. with frequencies with relative frequencies.

Graphical Displays of Data. with frequencies with relative frequencies.

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