Characteristic IR Absorption Frequencies of Organic Functional Groups

Functional
Type of
Characteristic
Intensity
Group
Vibration
Absorptions (cm-1)
Alcohol
O-H

(stretch, Hbonded)

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

=C-H

stretch

3010-3100

medium

=C-H

bending

675-1000

strong

C=C

stretch

1620-1680

variable

C-F

stretch

1000-1400

strong

C-Cl

stretch

600-800

strong

C-Br

stretch

500-600

strong

C-I

stretch

500

strong

stretch

3300

strong,sharp

stretch

2100-2260

variable, not present in symmetrical

alkynes

Alkene

Alkyl Halide

Alkyne
C-H

Amine
N-H

stretch

3300-3500

medium (primary amines have two

bands; secondary have one band, often
very weak)

C-N

stretch

1080-1360

medium-weak

N-H

bending

1600

medium

Aromatic
C-H

stretch

3000-3100

medium

C=C

stretch

1400-1600

medium-weak, multiple bands

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

Carbonyl
C=O

Detailed Information on Carbonyl IR

stretch

1670-1820

strong

(conjugation moves absorptions to lower wave numbers)

Ether

C-O

stretch

1000-1300 (10701150)

strong

stretch

2210-2260

medium

stretch

1515-1560 & 13451385

strong, two bands

Nitrile
CN
Nitro
N-O

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

Functional
Type of
Characteristic Absorptions
Intensity
Group
Vibration
(cm-1)
Carbonyl
C=O

stretch

1670-1820

strong

(conjugation moves absorptions to lower wave numbers)

Acid
C=O

stretch

1700-1725

strong

O-H

stretch

2500-3300

strong, very broad

C-O

stretch

1210-1320

strong

C=O

stretch

1740-1720

strong

=C-H

stretch

2820-2850 & 2720-2750

medium, two peaks

Amide
C=O

stretch

1640-1690

strong

N-H

stretch

3100-3500

unsubstituted have two

bands

N-H

bending

1550-1640

stretch

1800-1830 & 1740-1775

two bands

C=O

stretch

1735-1750

strong

C-O

stretch

1000-1300

two bands or more

Ketone
acyclic

stretch

1705-1725

strong

stretch

3-membered - 1850
4-membered - 1780
5-membered - 1745
6-membered - 1715
7-membered - 1705

strong

Aldehyde

Anhydride
C=O
Ester

cyclic

,-unsaturated

stretch

1665-1685

strong

aryl ketone

stretch

1680-1700

strong

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 S55
A more complete listing of functional group absorption frequencies ma be found
in: Nakanishi, Koji Infrared Absorption Spectroscopy. QD95.N383

Infrared Spectroscopy
1. Introduction
As noted in a previous chapter, the light our eyes see is but a small part of a broad
spectrum of electromagnetic radiation. On the immediate high energy side of the visible
spectrum lies the ultraviolet, and on the low energy side is the infrared. The portion of
the infrared region most useful for analysis of organic compounds is not immediately
adjacent to the visible spectrum, but is that having a wavelength range from 2,500 to
16,000 nm, with a corresponding frequency range from 1.9*1013 to 1.2*1014 Hz.

Photon energies associated with this part of the infrared (from 1 to 15 kcal/mole) are not
large enough to excite electrons, but may induce vibrational excitation of covalently
bonded atoms and groups. The covalent bonds in molecules are not rigid sticks or rods,
such as found in molecular model kits, but are more like stiff springs that can be
stretched and bent. The mobile nature of organic molecules was noted in the chapter
concerning conformational isomers. We must now recognize that, in addition to the facile
rotation of groups about single bonds, molecules experience a wide variety of vibrational
motions, characteristic of their component atoms. Consequently, virtually all organic
compounds will absorb infrared radiation that corresponds in energy to these vibrations.
Infrared spectrometers, similar in principle to the UV-Visible spectrometer described
elsewhere, permit chemists to obtain absorption spectra of compounds that are a unique
reflection of their molecular structure. An example of such a spectrum is that of the
flavoring agent vanillin, shown below.

The complexity of this spectrum is typical of most infrared spectra, and illustrates their
use in identifying substances. The gap in the spectrum between 700 & 800 cm -1 is due to
solvent (CCl4) absorption. Further analysis (below) will show that this spectrum also
indicates the presence of an aldehyde function, a phenolic hydroxyl and a substituted
benzene ring. The inverted display of absorption, compared with UV-Visible spectra, is
characteristic. Thus a sample that did not absorb at all would record a horizontal line at
100% transmittance (top of the
chart).
The frequency scale at the
Frequency - Wavelength Converter
bottom of the chart is given in
units of reciprocal centimeters
(cm-1) rather than Hz, because
Frequency in cm-1
the numbers are more
manageable. The reciprocal
Wavelength in
centimeter is the number of
wave cycles in one centimeter;
whereas, frequency in cycles
per second or Hz is equal to the number of wave cycles in 3*1010 cm (the distance
covered by light in one second). Wavelength units are in micrometers,microns (),
instead of nanometers for the same reason. Most infrared spectra are displayed on a
linear frequency scale, as shown here, but in some older texts a linear wavelength scale
is used. A calculator for interconverting these frequency and wavelength values is
provided on the right. Simply enter the value to be converted in the appropriate box,
press "Calculate" and the equivalent number will appear in the empty box.
Infrared spectra may be obtained from samples in all phases (liquid, solid and gaseous).
Liquids are usually examined as a thin film sandwiched between two polished salt plates
(note that glass absorbs infrared radiation, whereas NaCl is transparent). If solvents are
used to dissolve solids, care must be taken to avoid obscuring important spectral regions
by solvent absorption. Perchlorinated solvents such as carbon tetrachloride, chloroform
and tetrachloroethene are commonly used. Alternatively, solids may either be
incorporated in a thin KBr disk, prepared under high pressure, or mixed with a little nonvolatile liquid and ground to a paste (or mull) that is smeared between salt plates.

2. Vibrational Spectroscopy
A molecule composed of n-atoms has 3n degrees of freedom, six of which are
translations and rotations of the molecule itself. This leaves 3n-6 degrees of vibrational
freedom (3n-5 if the molecule is linear). Vibrational modes are often given descriptive
names, such as stretching, bending, scissoring, rocking and twisting. The four-atom
molecule of formaldehyde, the gas phase spectrum of which is shown below, provides
an example of these terms. If a ball & stick model of formaldehyde is not displayed to the
right of the spectrum, press the view ball&stick model button on the right. We expect six
fundamental vibrations (12 minus 6), and these have been assigned to the spectrum
absorptions. To see the formaldehyde molecule display a vibration, click one of the
buttons under the spectrum, or click on one of the absorption peaks in the spectrum.

Gas Phase Infrared Spectrum of Formaldehyde, H2C=O

View CH Asymmetric Stretch

2

Ball&Stick Model

View CH Symmetric Stretch

2

Spacefill Model

View C=O Stretch

Stick Model

View CH Scissoring
2

Motion Off

View CH Rocking
2
View CH Wagging
2

The exact frequency at which a given vibration occurs is determined by the strengths of
the bonds involved and the mass of the component atoms. For a more detailed
discussion of these factors Click Here. In practice, infrared spectra do not normally
display separate absorption signals for each of the 3n-6 fundamental vibrational modes
of a molecule. The number of observed absorptions may be increased by additive and
subtractive interactions leading to combination tones and overtones of the fundamental
vibrations, in much the same way that sound vibrations from a musical instrument
interact. Furthermore, the number of observed absorptions may be decreased by
molecular symmetry, spectrometer limitations, and spectroscopic selection rules. One
selection rule that influences the intensity of infrared absorptions, is that a change in
dipole moment should occur for a vibration to absorb infrared energy. Absorption bands
associated with C=O bond stretching are usually very strong because a large change in
the dipole takes place in that mode.
Some General Trends:
i) Stretching frequencies are higher than corresponding bending frequencies. (It is
easier to bend a bond than to stretch or compress it.)
ii) Bonds to hydrogen have higher stretching frequencies than those to heavier
atoms.
iii) Triple bonds have higher stretching frequencies than corresponding double
bonds, which in turn have higher frequencies than single bonds.
(Except for bonds to hydrogen).

The general regions of the infrared spectrum in which various kinds of vibrational bands
are observed are outlined in the following chart. Note that the blue colored sections
above the dashed line refer to stretching vibrations, and the green colored band below
the line encompasses bending vibrations. The complexity of infrared spectra in the 1450
to 600 cm-1 region makes it difficult to assign all the absorption bands, and because of
the unique patterns found there, it is often called the fingerprint region. Absorption

bands in the 4000 to 1450 cm -1 region are usually due to stretching vibrations of diatomic
units, and this is sometimes called the group frequency region.

3. Group Frequencies
Detailed information about the infrared absorptions observed for various bonded atoms
and groups is usually presented in tabular form. The following table provides a collection
of such data for the most common functional groups. Following the color scheme of the
chart, stretching absorptions are listed in the blue-shaded section and bending
absorptions in the green shaded part. More detailed descriptions for certain groups
(e.g. alkenes, arenes, alcohols, amines & carbonyl compounds) may be viewed by
clicking on the functional class name. Since most organic compounds have C-H
bonds, a useful rule is that absorption in the 2850 to 3000 cm -1 is due to sp3 C-H
stretching; whereas, absorption above 3000 cm-1 is from sp2 C-H stretching or sp C-H
stretching if it is near 3300 cm -1.

Typical Infrared Absorption Frequencies

Functional Class

Stretching Vibrations

Bending Vibrations

Inten
sity

Range Inten
Assignment
(cm-1) sity

Range (cm-1)

Assignment

Alkanes

2850-3000

str

CH3, CH2 & CH

2 or 3 bands

13501470
13701390
720725

med
med
wk

CH2 &
CH3 deformati
on
CH3 deformati
on
CH2 rocking

Alkenes

3020-3100
1630-1680

med
var
str

880995
780850
675-

str
med
med

1900-2000

=C-H &
=CH2 (usually
sharp)
C=C (symmetry
reduces intensity)

=C-H & =CH2

(out-of-plane
bending)
cisRCH=CHR

730
C=C asymmetric
stretch
Alkynes

3300
2100-2250

str
var

Arenes

3030
1600 & 1500

Alcohols &
Phenols

Amines

Aldehydes &
Ketones

str

C-H
deformation

var
C-H (may be several 690med- bands)
900
wk
C=C (in ring) (2
bands)
(3 if conjugated)

strmed

C-H bending
&
ring puckering

3580-3650
3200-3550
970-1250

var
str
str

O-H (free), usually

sharp
O-H (H-bonded),
usually broad
C-O

13301430
650770

med
varwk

O-H bending
(in-plane)
O-H bend
(out-of-plane)

3400-3500 (dil.
soln.)
3300-3400 (dil.
soln.)
1000-1250

wk
wk
med

N-H (1-amines), 2
bands
N-H (2-amines)
C-N

15501650
660900

med- NH2 scissorin

str
g (1-amines)
var
NH2 & N-H
wagging
(shifts on Hbonding)

13501360
14001450
1100

str
str
med

CH3 bending
CH2 bending
C-C-C
bending

13951440

med

C-O-H
bending

2690-2840(2 bands) med

1720-1740
str
1710-1720
str
1690
1675
1745
1780

2500-3300 (acids)
Carboxylic
Acids & Derivati overlap C-H
1705-1720 (acids)
ves
1210-1320 (acids)
1785-1815 (
acyl halides)
1750 &
1820
(anhydrides)
10401100
1735-1750
(esters)
10001300
16301695(amide
s)

str
str
str
str

C-H (usually sharp) 600CC (symmetry

700
reduces intensity)

C-H (aldehyde C-H)

C=O (saturated
aldehyde)
C=O (saturated
ketone)
aryl ketone
, -unsaturation
cyclopentanone
cyclobutanone

str
str
medstr

O-H (very broad)

C=O (H-bonded)
O-C (sometimes 2peaks)

str
str
str
str
str
str

C=O
C=O (2-bands)
O-C
C=O
O-C (2-bands)
1590C=O (amide I band) 1650
15001560

med
med

N-H (1amide) II band

N-H (2amide) II band

2240-2260

med

CN (sharp)

Isocyanates,Isot 2100-2270
hiocyanates,
Diimides, Azides
& Ketenes

med

-N=C=O, -N=C=S
-N=C=N-, -N3,
C=C=O

Nitriles

To illustrate the usefulness of infrared absorption spectra, examples for five C4H8O
isomers are presented below their corresponding structural formulas. The five spectra
may be examined in turn by clicking the "Toggle Spectra" button. Try to associate each
spectrum (A - E) with one of the isomers in the row above it. When you have made
assignments check your answers by clicking on the structure or name of each isomer.

4. Other Functional Groups

Infrared absorption data for some functional groups not listed in the preceding table are
given below. Most of the absorptions cited are associated with stretching vibrations.
Standard abbreviations (str = strong, wk = weak, brd = broad & shp = sharp) are used to
describe the absorption bands.
Functional Class

Characteristic Absorptions
Sulfur Functions

S-H thiols

2550-2600 cm-1 (wk & shp)

S-OR esters

700-900 (str)

S-S disulfide

500-540 (wk)

C=S thiocarbonyl

1050-1200 (str)

S=O sulfoxide
sulfone
sulfonic acid
sulfonyl chloride
sulfate

1030-1060 (str)
1325 25 (as) & 1140 20 (s) (both str)
1345 (str)
1365 5 (as) & 1180 10 (s) (both str)
1350-1450 (str)

Phosphorous Functions
P-H phosphine

2280-2440 cm-1 (med & shp)

950-1250 (wk) P-H bending

(O=)PO-H phosphonic acid

2550-2700 (med)

P-OR esters

900-1050 (str)

P=O phosphine oxide

phosphonate
phosphate
phosphoramide

1100-1200 (str)
1230-1260 (str)
1100-1200 (str)
1200-1275 (str)
Silicon Functions

Si-H silane

2100-2360 cm-1 (str)

Si-OR

1000-11000 (str & brd)

Si-CH3

1250 10 (str & shp)

Oxidized Nitrogen Functions

=NOH oxime
O-H (stretch)
C=N
N-O

3550-3600 cm-1 (str)

1665 15
945 15

N-O amine oxide

aliphatic
aromatic

960 20
1250 50

N=O nitroso
nitro

1550 50 (str)
1530 20 (as) & 1350 30 (s)

Test your ability to use information from infrared and mass spectrometry to identify an
unknown compound. Clicking the button opens a display in which four different problems
of this kind may be selected. Answers are provided once an effort to solve the problem
has been made.

An infrared spectroscopy correlation table (or table of infrared absorption frequencies) is a list
of absorption peaks and frequencies, typically reported in wavenumber, for common types
[1][2]
ofmolecular bonds and functional groups.
In physical and analytical chemistry, infrared
spectroscopy (IR spectroscopy) is a technique used to identify chemical compounds based on the
wayinfrared radiation is absorbed by the compound.
The absorptions in this range do not apply only to bonds in organic molecules. IR spectroscopy is
useful when it comes to analysis of inorganic compounds (such as metal complexes or
[3]
fluoromanganates) as well. Phosphonates could also be characterized by two middle-sized bands
1
between 2300 and 2400 cm .
Tables of vibrational transitions of stable

Bond

Type of bond

[4]

and transient molecules

Specific type of bond

[5]

are also available.

Absorption peak
-1
cm (nm)

1260 cm
nm)

1380 cm
nm)

(7937

(7246

Appearance

strong

weak

methyl
2870 cm
nm)

2960 cm
nm)
CH

(3484

(3378

medium to strong

medium to strong

alkyl
1470 cm
nm)

methylene

2850 cm
nm)

2925 cm
nm)

methine

2890 cm
nm)

(6803

(3509

(3419

(3460

strong

medium to strong

medium to strong

weak

900 cm
nm)

CCH2

2975 cm
nm)

3080 cm
nm)

CCH

3020 cm
nm)

900 cm
nm)

vinyl

(11111

(3361

(3247

(3311

(11111

strong

medium

medium

medium

strong

monosubstituted alkenes
990 cm
nm)

(10101

cis-disubstituted alkenes

670
1
700 cm (1428614925 nm)

trans-disubstituted
alkenes

965 cm
nm)

trisubstituted alkenes

800
1
840 cm (1190512500 nm)

benzene/sub. benzene

3070 cm
nm)

monosubstituted
benzene

700
1
750 cm (1333314286 nm)

(10363

(3257

strong

strong

strong

strong to medium

weak

aromatic
strong

690
1
710 cm (1408514493 nm)

ortho-disub. benzene

750 cm
nm)

(13333

strong

strong

750
1
800 cm (1250013333 nm)

strong

860
1
900 cm (1111111628 nm)

strong

para-disub. benzene

800
1
860 cm (1162812500 nm)

strong

any

3300 cm
nm)

meta-disub. benzene

alkynes

2720 cm
nm)
aldehydes

acyclic CC

(3030

medium

monosub. alkenes

1645 cm
nm)

1,1-disub. alkenes

1655 cm
nm)

cis-1,2-disub. alkenes

medium

(3676

any
2820 cm
nm)

CC

1660 cm

(3546

(6079

(6042

(6024

medium

medium

medium

nm)

trans-1,2-disub. alkenes

1675 cm
nm)

trisub., tetrasub. alkenes

1670 cm
nm)

1600 cm
nm)

(5970

(5988

(6250

medium

weak

strong

conjugated CC
1650 cm
nm)

(6061

strong

dienes
with benzene ring

1625 cm
nm)

with CO

1600 cm
nm)

CC (both sp )

any

(6154

(6250

1640
1
1680 cm (59526098 nm)

1450 cm
nm)

1500 cm
nm)
aromatic CC

strong

strong

medium

(6897

(6667
weak to strong
(usually 3 or 4)

any
1580 cm
nm)

1600 cm
nm)

(6329

(6250

terminal alkynes

2100
1
2140 cm (46734762 nm)

weak

disubst. alkynes

2190
1
2260 cm (44254566 nm)

very weak (often

indisinguishable)

saturated aliph./cyclic 6membered

1720 cm
nm)

,-unsaturated

1685 cm
nm)

aromatic ketones

1685 cm
nm)

cyclic 5-membered

1750 cm
nm)

cyclic 4-membered

1775 cm
nm)

aldehydes

1725 cm
nm)

saturated carboxylic
acids

1710 cm
nm)

unsat./aromatic carb.
acids

1680
1
1690 cm (59175952 nm)

CC

(5814

(5935

(5935

aldehyde/ketone

CO

carboxylic
acids/derivates

esters and lactones

1735 cm

(5714

(5634

(5797

influence of
conjugation (as with
ketones)

(5848

(5764

influenced by
conjugation and ring

nm)

1760 cm
nm)

size (as with

ketones)

(5682

anhydrides
1820 cm
nm)

(5495

acyl halides

1800 cm
nm)

amides

1650 cm
nm)

carboxylates (salts)

1550
1
1610 cm (62116452 nm)

amino acid zwitterions

1550
1
1610 cm (62116452 nm)

low concentration

3610
1
3670 cm (27252770 nm)

high concentration

3200
1
3400 cm (29413125 nm)

low concentration

3500
1
3560 cm (28092857 nm)

(5556

(6061

associated amides

alcohols, phenols

OH

carboxylic acids

high concentration

3000 cm

(3333

broad

broad

nm)

primary amines

3400
1
3500 cm (28572941 nm)

strong

1560
1
1640 cm (60986410 nm)

strong

any

NH
secondary
amines

ammonium ions

alcohols

>3000 cm
nm)

any

2400
1
3200 cm (31254167 nm)

multiple broad
peaks

primary

1040
1
1060 cm (94349615 nm)

strong, broad

secondary

~1100 cm
nm)

tertiary

1150
1
1200 cm (83338696 nm)

any

1200 cm
nm)

aliphatic

1120 cm
nm)

CO

phenols

any

(>3333

(~9091

(8333

(8929

ethers
aromatic

1220
1
1260 cm (7937-

weak to medium

strong

medium

8197 nm)

carboxylic acids

esters

aliphatic amines

CN

CN

any

1100
1
1300 cm (76929091 nm)

two bands (distinct

from ketones, which
do not possess a
CO bond)

any

1020
1
1220 cm (81979804 nm)

often overlapped

any

1615
1
1700 cm (58826192 nm)

similar conjugation
effects to CO

unconjugated

2250 cm
nm)

conjugated

2230 cm
nm)

any

2165
1
2110 cm (47394619 nm)

any

2140
1
1990 cm (50254673 nm)

ordinary

1000
1
1100 cm (909110000 nm)

(4444

medium

CN (nitriles)

RNC
(isocyanides)

RNCS

CX

any

1250
1
1300 cm (76928000 nm)

fluoroalkanes

(4484

medium

trifluromethyl

1100
1
1200 cm (83339091 nm)

two strong, broad

bands

chloroalkanes

any

540
1
760 cm (1315818519 nm)

weak to medium

bromoalkanes

any

500
1
600 cm (1666720000 nm)

medium to strong

iodoalkanes

any

500 cm
nm)

1540 cm
nm)

(20000

(6494

medium to strong

stronger

aliphatic

NO

1380 cm
nm)

nitro compounds

aromatic

(7246

1520,
1
1350 cm (74076579 nm)

weaker

lower if conjugated