43
The C=O stretching frequency aldehydes and ketones
The C=O stretching frequency
aldehydes and ketones
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
10
20
30
40
50
60
70
80
90
100
H-C=OImpurity peak,probably O-H
Figure IR-14. Butanal, neat liquid, thin film: CH3 CH2 CH2 CHO
Aliphatic Aldehyde
1730 cm-1
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
0
20
40
60
80
100
Figure IR-35. 5-Hexene-2-one, neat liquid: CH2 =CH2 CH2 CH2 COCH3
Aliphatic Ketone
1715 cm-1
The C=O stretching frequency
esters
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
0
20
40
60
80
100
Top: CHCl3 vs CHCl3
Bottom: 2.5 % v/v un CHCl3
Aliphatic Ester
Figure IR-33. Methyl acetate in 0.1 mm NaCl cells: CH3 CO2 CH3
1720 cm-1
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
0
20
40
60
80
100
Top: CHCl3 vs CHCl3
Bottom: 2.5 % v/v un CHCl3
CCl4 neat1746 cm-1
1748 cm-1
1720 cm-1
Wavenumber, cm-1
1000150020002500300035004000
% T
rans
mitt
ance
0
20
40
60
80
100
120
liquid film
vapor: 106 °C
Figure IR-34. Vapor and liquid spectra of ethyl n-hexanoate: CH3 CH2 CH2 CH2 CH2 CO2 CH2 CH3
Aliphatic EsterThe effect of phase on IR frequencies
The C=O stretching frequency
aliphatic acids
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
Aliphatic Acid
Figure IR-26. The liquid,
vapor and CCl4 soln
spectra of hexanoic acid:
CH3 (CH2 )4 CO2 H
Wavenumber, cm-1
1000150020002500300035004000
% T
rans
mitt
ance
0
20
40
60
80
100
120
liquid film
vapor: 134 °C
1710 cm-1
The C=O stretching frequency
aliphatic amides
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
Amide I 1662 cm-1
Amide II; 1634 cm-1
KBr pellet
Wavnumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
10
20
30
40
50
60
70
80
90
100
Amide I Amide II
Figure IR-21. N-Methyl acetamide, neat liquid; thin film: CH3 CONHCH3
Secondary Amide
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
0
20
40
60
80
100
Figure IR-23. N,N-Dimethylacetamide, neat liquid; thin film: CH3 CON(CH3 )2
Tertiary Amide
No amide II band
The C=O stretching frequency
anhydrides
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
Wavenumber, cm-1
50010001500200025003000350040004500
% T
rans
mitt
ance
0
20
40
60
80
100
Figure IR-36. Propionic anhydride, neat liquid: CH3 CH2 CO2 COCH2 CH3
Anhydrides
The C=O stretching frequency
carboxylates
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
1410 cm-11560 cm-1
The C=C bond stretch
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
0
20
40
60
80
100
HC=Cstretches
CH3,CH2 symmetric and asymmetric stretches
C=Cstretch
CH3,CH2 bending vibrations
(CH2)4
rocking
out of plane H wag of vinylgroup 900, 1000 cm-1)
Figure IR-9. 1-Heptene; neat sample, thin film:
H2 C=CH-CH2 CH2 CH2 CH2 CH3
The C=C bond stretch when next to a heteroatom
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
0
20
40
60
80
100
Figure IR-40. 2,5-Dimethoxy2,5-dihydrofuran, neat liquid:
O OCH3CH3O
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
0
20
40
60
80
100
Figure IR-41. 2,3-Dihydrofuran, neat liquid:O
1610 cm-1
1652 cm-1
The cumulative C=C bond stretch
1958 cm-1
The NO2 stretching frequency
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
N
O
O
+N
O
O
+-
-
1556 cm-1 1367 cm-1
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
0
20
40
60
80
100
120
symmetric and asymmetric-NO2 stretch
4-Chloro-2-nitrophenol, KBr pellet:
1510 and 1320 cm-1
Aromatic Rings
Ring breathing motions
1600-1585
1500-1400
Both often appear as doublets
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
0
20
40
60
80
100
carbon-carbontriple bond stretch
H
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
20
30
40
50
60
70
80
90
overtones of the benzene ring
Benzene, neat, thin film:
![Aqueous-biphasic hydroformylation of 1-hexene catalyzed … · Aqueous-biphasic hydroformylation of 1-hexene catalyzed by the complex HCo(CO)[P(o-C 6 H 4 SO 3 Na)] 3 129 system which](https://static.documents.pub/doc/80x56/5b3648607f8b9aad388ce1b6/aqueous-biphasic-hydroformylation-of-1-hexene-catalyzed-aqueous-biphasic-hydroformylation.jpg)
