Analysis of Infrared spectroscopy
Infrared spectroscopy (IR) is an ideal technique to analyze chemical structural properties of natural materials, since the frequencies of several vibrational modes of organic and inorganic molecules are active in the infrared. This method has become one of the major analytical techniques used because of its quality screening, quickness, and cost of analysis.
Compounds with a dipole moment selectively absorb IR radiation according to their characteristic functional groups—hydroxyl, nitirle, amide, for example. An IR spectrogram plots the absorbance versus the wavelengths ranging from 700 to 400 000 nm and wave numbers from 14 000 to 25 cm−1. As the compounds absorb energy the molecule vibrates more–stretching and bending–depending on its geometry.
The pattern of the absorption spectrum is like a fingerprint that identifies the molecule, which lends itself to both quantitative and qualitative analysis. The IR absorption frequency depends on the vibrational modes, whereas the intensity depends on: (a) how effectively energy is transferred to the molecule, which depends on the change in the dipole moment that occurs during the molecular vibration, (b) how much is transmitted (or reflected), and (c) the detector.
Fig 1. Range of IR spectroscopic stretching bands
IR SPECTRUM TABLE BY FREQUENCY RANGE
Frequency Range | Absorption (cm-1) | Appearance | Group | Compound Class | Comments |
---|---|---|---|---|---|
4000-3000 cm-1 | 3700-3584 | medium, sharp | O-H stretching | alcohol | free |
3550-3200 | strong, broad | O-H stretching | alcohol | intermolecular bonded | |
3500 | medium | N-H stretching | primary amine | ||
3400 | |||||
3400-3300 | medium | N-H stretching | aliphatic primary amine | ||
3330-3250 | |||||
3350-3310 | medium | N-H stretching | secondary amine | ||
3300-2500 | strong, broad | O-H stretching | carboxylic acid | usually centered on 3000 cm-1 | |
3200-2700 | weak, broad | O-H stretching | alcohol | intramolecular bonded | |
3000-2800 | strong, broad | N-H stretching | amine salt | ||
3000-2500 cm-1 | |||||
3000-2500 cm-1 | 3333-3267 | strong, sharp | C-H stretching | alkyne | |
3100-3000 | medium | C-H stretching | alkene | ||
3000-2840 | medium | C-H stretching | alkane | ||
2830-2695 | medium | C-H stretching | aldehyde | doublet | |
2600-2550 | weak | S-H stretching | thiol | ||
2400-2000 cm-1 | |||||
2400-2000 cm-1 | 2349 | strong | O=C=O stretching | carbon dioxide | |
2275-2250 | strong, broad | N=C=O stretching | isocyanate | ||
2260-2222 | weak | CΞN stretching | nitrile | ||
2260-2190 | weak | CΞC stretching | alkyne | disubstituted | |
2175-2140 | strong | S-CΞN stretching | thiocyanate | ||
2160-2120 | strong | N=N=N stretching | azide | ||
2150 | C=C=O stretching | ketene | |||
2145-2120 | strong | N=C=N stretching | carbodiimide | ||
2140-2100 | weak | CΞC stretching | alkyne | monosubstituted | |
2140-1990 | strong | N=C=S stretching | isothiocyanate | ||
2000-1900 | medium | C=C=C stretching | allene | ||
2000 | C=C=N stretching | ketenimine | |||
2000-1650 cm-1 | |||||
2000-1650 cm-1 | 2000-1650 | weak | C-H bending | aromatic compound | overtone |
1870-1540 | |||||
1818 | strong | C=O stretching | anhydride | ||
1750 | |||||
1815-1785 | strong | C=O stretching | acid halide | ||
1800-1770 | strong | C=O stretching | conjugated acid halide | ||
1775 | strong | C=O stretching | conjugated anhydride | ||
1720 | |||||
1770-1780 | strong | C=O stretching | vinyl / phenyl ester | ||
1760 | strong | C=O stretching | carboxylic acid | monomer | |
1750-1735 | strong | C=O stretching | esters | 6-membered lactone | |
1750-1735 | strong | C=O stretching | δ-lactone | γ: 1770 | |
1745 | strong | C=O stretching | cyclopentanone | ||
1740-1720 | strong | C=O stretching | aldehyde | ||
1730-1715 | strong | C=O stretching | α,β-unsaturated ester | or formates | |
1725-1705 | strong | C=O stretching | aliphatic ketone | or cyclohexanone or cyclopentenone | |
1720-1706 | strong | C=O stretching | carboxylic acid | dimer | |
1710-1680 | strong | C=O stretching | conjugated acid | dimer | |
1710-1685 | strong | C=O stretching | conjugated aldehyde | ||
1690 | strong | C=O stretching | primary amide | free (associated: 1650) | |
1690-1640 | medium | C=N stretching | imine / oxime | ||
1685-1666 | strong | C=O stretching | conjugated ketone | ||
1680 | strong | C=O stretching | secondary amide | free (associated: 1640) | |
1680 | strong | C=O stretching | tertiary amide | free (associated: 1630) | |
1650 | strong | C=O stretching | δ-lactam | γ: 1750-1700 β: 1760-1730 | |
1670-1600 cm-1 | |||||
1670-1600 cm-1 | 1678-1668 | weak | C=C stretching | alkene | disubstituted (trans) |
1675-1665 | weak | C=C stretching | alkene | trisubstituted | |
1675-1665 | weak | C=C stretching | alkene | tetrasubstituted | |
1662-1626 | medium | C=C stretching | alkene | disubstituted (cis) | |
1658-1648 | medium | C=C stretching | alkene | vinylidene | |
1650-1600 | medium | C=C stretching | conjugated alkene | ||
1650-1580 | medium | N-H bending | amine | ||
1650-1566 | medium | C=C stretching | cyclic alkene | ||
1648-1638 | strong | C=C stretching | alkene | monosubstituted | |
1620-1610 | strong | C=C stretching | α,β-unsaturated ketone | ||
1600-1300 cm-1 | |||||
1600-1300 cm-1 | 1550-1500 | strong | N-O stretching | nitro compound | |
1372-1290 | |||||
1465 | medium | C-H bending | alkane | methylene group | |
1450 | medium | C-H bending | alkane | methyl group | |
1375 | |||||
1390-1380 | medium | C-H bending | aldehyde | ||
1385-1380 | medium | C-H bending | alkane | gem dimethyl | |
1370-1365 | |||||
1400-1000 cm-1 | |||||
1400-1000 cm-1 | 1440-1395 | medium | O-H bending | carboxylic acid | |
1420-1330 | medium | O-H bending | alcohol | ||
1415-1380 | strong | S=O stretching | sulfate | ||
1200-1185 | |||||
1410-1380 | strong | S=O stretching | sulfonyl chloride | ||
1204-1177 | |||||
1400-1000 | strong | C-F stretching | fluoro compound | ||
1390-1310 | medium | O-H bending | phenol | ||
1372-1335 | strong | S=O stretching | sulfonate | ||
1195-1168 | |||||
1370-1335 | strong | S=O stretching | sulfonamide | ||
1170-1155 | |||||
1350-1342 | strong | S=O stretching | sulfonic acid | anhydrous | |
1165-1150 | hydrate: 1230-1120 | ||||
1350-1300 | strong | S=O stretching | sulfone | ||
1160-1120 | |||||
1342-1266 | strong | C-N stretching | aromatic amine | ||
1310-1250 | strong | C-O stretching | aromatic ester | ||
1275-1200 | strong | C-O stretching | alkyl aryl ether | ||
1075-1020 | |||||
1250-1020 | medium | C-N stretching | amine | ||
1225-1200 | strong | C-O stretching | vinyl ether | ||
1075-1020 | |||||
1210-1163 | strong | C-O stretching | ester | ||
1205-1124 | strong | C-O stretching | tertiary alcohol | ||
1150-1085 | strong | C-O stretching | aliphatic ether | ||
1124-1087 | strong | C-O stretching | secondary alcohol | ||
1085-1050 | strong | C-O stretching | primary alcohol | ||
1070-1030 | strong | S=O stretching | sulfoxide | ||
1050-1040 | strong, broad | CO-O-CO stretching | anhydride | ||
1000-650 cm-1 | |||||
1000-650 cm-1 | 995-985 | strong | C=C bending | alkene | monosubstituted |
915-905 | |||||
980-960 | strong | C=C bending | alkene | disubstituted (trans) | |
895-885 | strong | C=C bending | alkene | vinylidene | |
850-550 | strong | C-Cl stretching | halo compound | ||
840-790 | medium | C=C bending | alkene | trisubstituted | |
730-665 | strong | C=C bending | alkene | disubstituted (cis) | |
690-515 | strong | C-Br stretching | halo compound | ||
600-500 | strong | C-I stretching | halo compound | ||
900-700 cm-1 | |||||
900-700 cm-1 | 880 ± 20 | strong | C-H bending | 1,2,4-trisubstituted | |
810 ± 20 | |||||
880 ± 20 | strong | C-H bending | 1,3-disubstituted | ||
780 ± 20 | |||||
(700 ± 20) | |||||
810 ± 20 | strong | C-H bending | 1,4-disubstituted or | ||
1,2,3,4-tetrasubstituted | |||||
780 ± 20 | strong | C-H bending | 1,2,3-trisubstituted | ||
(700 ± 20) | |||||
755 ± 20 | strong | C-H bending | 1,2-disubstituted | ||
750 ± 20 | strong | C-H bending | monosubstituted | ||
700 ± 20 | benzene derivative |
Compound Class | Group | Absorption (cm-1) | Appearance | Comments |
---|---|---|---|---|
acid halide | C=O stretching | 1815-1785 | strong | |
alcohols | O-H stretching | 3700-3584 | medium, sharp | free |
O-H stretching | 3550-3200 | strong, broad | intermolecular bonded | |
O-H stretching | 3200-2700 | weak, broad | intramolecular bonded | |
O-H bending | 1420-1330 | medium | ||
aldehyde | C-H stretching | 2830-2695 | medium | doublet |
C=O stretching | 1740-1720 | strong | ||
C-H bending | 1390-1380 | medium | ||
aliphatic ether | C-O stretching | 1150-1085 | strong | |
aliphatic ketone | C=O stretching | 1725-1705 | strong | or cyclohexanone or cyclopentenone |
aliphatic primary amine | N-H stretching | 3400-3300 | medium | |
alkane | C-H stretching | 3000-2840 | medium | |
C-H bending | 1465 | medium | methylene group | |
C-H bending | 1450 | medium | methyl group | |
C-H bending | 1385-1380 | medium | gem dimethyl | |
C-H stretching | 3100-3000 | medium | ||
C=C stretching | 1678-1668 | weak | disubstituted (trans) | |
C=C stretching | 1675-1665 | weak | trisubstituted | |
C=C stretching | 1675-1665 | weak | tetrasubstituted | |
C=C stretching | 1662-1626 | medium | disubstituted (cis) | |
C=C stretching | 1658-1648 | medium | vinylidene | |
C=C stretching | 1648-1638 | strong | monosubstituted | |
C=C bending | 995-985 | strong | monosubstituted | |
C=C bending | 980-960 | strong | disubstituted (trans) | |
C=C bending | 895-885 | strong | vinylidene | |
C=C bending | 840-790 | medium | trisubstituted | |
C=C bending | 730-665 | strong | disubstituted (cis) | |
alkyl aryl ether | C-O stretching | 1275-1200 | strong | |
alkyne | C-H stretching | 3333-3267 | strong, sharp | |
CΞC stretching | 2260-2190 | weak | disubstituted | |
CΞC stretching | 2140-2100 | weak | monosubstituted | |
allene | C=C=C stretching | 2000-1900 | medium | |
amine | N-H bending | 1650-1580 | medium | |
C-N stretching | 1250-1020 | medium | ||
amine salt | N-H stretching | 3000-2800 | strong, broad | |
anhydride | C=O stretching | 1818 | strong | |
CO-O-CO stretching | 1050-1040 | strong, broad | ||
aromatic amine | C-N stretching | 1342-1266 | strong | |
aromatic compound | C-H bending | 2000-1650 | weak | overtone |
aromatic ester | C-O stretching | 1310-1250 | strong | |
azide | N=N=N stretching | 2160-2120 | strong | |
benzene derivative | 700 ± 20 | |||
carbodiimide | N=C=N stretching | 2145-2120 | strong | |
carbon dioxide | O=C=O stretching | 2349 | strong | |
carboxylic acid | O-H stretching | 3300-2500 | strong, broad | usually centered on 3000 cm-1 |
C=O stretching | 1760 | strong | monomer | |
C=O stretching | 1720-1706 | strong | dimer | |
O-H bending | 1440-1395 | medium | ||
conjugated acid | C=O stretching | 1710-1680 | strong | dimer |
conjugated acid halide | C=O stretching | 1800-1770 | strong | |
conjugated aldehyde | C=O stretching | 1710-1685 | strong | |
conjugated alkene | C=C stretching | 1650-1600 | medium | |
conjugated anhydride | C=O stretching | 1775 | strong | |
conjugated ketone | C=O stretching | 1685-1666 | strong | |
cyclic alkene | C=C stretching | 1650-1566 | medium | |
cyclopentanone | C=O stretching | 1745 | strong | |
ester | C-O stretching | 1210-1163 | strong | |
esters | C=O stretching | 1750-1735 | strong | 6-membered lactone |
fluoro compound | C-F stretching | 1400-1000 | strong | |
halo compound | C-Cl stretching | 850-550 | strong | |
C-Br stretching | 690-515 | strong | ||
C-I stretching | 600-500 | strong | ||
imine / oxime | C=N stretching | 1690-1640 | medium | |
isocyanate | N=C=O stretching | 2275-2250 | strong, broad | |
isothiocyanate | N=C=S stretching | 2140-1990 | strong | |
ketene | C=C=O stretching | 2150 | ||
ketenimine | C=C=N stretching | 2000 | ||
monosubstituted | C-H bending | 750 ± 20 | strong | |
nitrile | CΞN stretching | 2260-2222 | weak | |
nitro compound | N-O stretching | 1550-1500 | strong | |
none | 3330-3250 | |||
none | 1870-1540 | |||
none | 1750 | |||
none | 1720 | |||
none | 1372-1290 | |||
none | 1375 | |||
none | 1370-1365 | |||
none | 1200-1185 | |||
none | 1204-1177 | |||
none | 1195-1168 | |||
none | 1170-1155 | |||
none | 1165-1150 | hydrate: 1230-1120 | ||
none | 1160-1120 | |||
none | 1075-1020 | |||
none | 1075-1020 | |||
none | 915-905 | |||
none | 810 ± 20 | |||
none | 780 ± 20 | |||
none | (700 ± 20) | |||
none | (700 ± 20) | |||
phenol | O-H bending | 1390-1310 | medium | |
primary alcohol | C-O stretching | 1085-1050 | strong | |
primary amide | C=O stretching | 1690 | strong | free (associated: 1650) |
N-H stretching | 3500 | medium | ||
secondary alcohol | C-O stretching | 1124-1087 | strong | |
secondary amide | C=O stretching | 1680 | strong | free (associated: 1640) |
secondary amine | N-H stretching | 3350-3310 | medium | |
sulfate | S=O stretching | 1415-1380 | strong | |
sulfonamide | S=O stretching | 1370-1335 | strong | |
sulfonate | S=O stretching | 1372-1335 | strong | |
sulfone | S=O stretching | 1350-1300 | strong | |
sulfonic acid | S=O stretching | 1350-1342 | strong | anhydrous |
sulfonyl chloride | S=O stretching | 1410-1380 | strong | |
sulfoxide | S=O stretching | 1070-1030 | strong | |
tertiary alcohol | C-O stretching | 1205-1124 | strong | |
tertiary amide | C=O stretching | 1680 | strong | free (associated: 1630) |
thiocyanate | S-CΞN stretching | 2175-2140 | strong | |
thiol | S-H stretching | 2600-2550 | weak | |
vinyl / phenyl ester | C=O stretching | 1770-1780 | strong | |
vinyl ether | C-O stretching | 1225-1200 | strong | |
α,β-unsaturated ester | C=O stretching | 1730-1715 | strong | or formates |
α,β-unsaturated ketone | C=C stretching | 1620-1610 | strong | |
δ-lactam | C=O stretching | 1650 | strong | γ: 1750-1700 β: 1760-1730 |
δ-lactone | C=O stretching | 1750-1735 | strong | γ: 1770 |
1,2,3,4-tetrasubstituted | ||||
1,2,3-trisubstituted | C-H bending | 780 ± 20 | strong | |
C-H bending | 880 ± 20 | strong | ||
1,2-disubstituted | C-H bending | 755 ± 20 | strong | |
C-H bending | 880 ± 20 | strong | ||
1,4-disubstituted or | C-H bending | 810 ± 20 | strong |