[PDF] The C=O stretching frequency





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IR – Spectroscopy ketone carbonyls have slightly lower stretching frequencies, Why the wavenumber of I amide band is usualy below 1700 cm-1 ?




AMIDES AND AMINES - Springer

F S Parker, Applications of Infrared Spectroscopy in Biochemistry, Biology, the characteristic frequencies of amides in the region - 700-300 cm - 1

[PDF] The C=O stretching frequency

The C=O stretching frequency amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R Aliphatic Ester The effect of phase on IR frequencies 

[PDF] Infrared spectra of N-monoaryl amides - CORE

Page INTRODUCTION 1 ORIGIN AND SIGNIFICANCE OF GROUP FREQUENCIES 2 EXPERIMENTAL 21 THE NH STRETCHING REGION 57 THE AMIDE I BAND

[PDF] S5 Tables IR

V-Agdal/Faculté des Sciences/SMC5/SPECTROSCOPIE / TABLES IR Amide secondaire ⎩ N B : Ces plages de fréquence sont données à titre indicatif

AMIDES AND AMINES

F S Parker, Applications of Infrared Spectroscopy in Biochemistry, Biology, and the characteristic frequencies of amides in the region - 700-300 cm - 1

[PDF] The C=O stretching frequency

The C=O stretching frequency The effect of phase on IR frequencies Amide I Amide II Figure IR-21 N-Methyl acetamide, neat liquid; thin film: CH 3

[PDF] Spectroscopie infrarouge - AC Nancy Metz

Les transitions entre niveaux de rotation apparaissent dans l'I R lointain (de 20 à 250 auront une fréquence d'élongation plus élevée que celle a deux bandes pour les amides primaires (élongations symétrique et asymétrique) (ici

[PDF] Ir lecture part 2

indicates either an aldehyde, ketone, carboxylic acid, ester, amide, anhydride cyclic ketones The bond angle influences the absorption frequency of the C=O

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[PDF] The C=O stretching frequency 8014_3lectureIR2.pdf

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(CO 2 )R 1750-1735 S(sh) 33, 34 carboxylic acids RCO 2

H 1720-1680 S(sh) 26,27,30

amides (Amide I) RCONH 2 , RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH 2 1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR 2 1650-1620 S(sh) 23
anhydrides R(CO 2

CO)R 1820, 1750 S, S(sh) 36

carboxylates R(CO 2 ) - , M + 1600, 1400 S,S(sh) 42

C=C olefins R

2 C=CR 2 1680-1640 W(sh) 10, 39, 40
R 2 C=CH 2 1600-1675 M(sh) 9, 35
R 2

C=C(OR)R 1600-1630 S(sh) 41

-NO 2 nitro groups RNO 2 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

% Transmittance

102030405060708090100

H-C=O

Impurity peak,

probably O-H Figure IR-14. Butanal, neat liquid, thin film: CH 3 CH 2 CH 2 CHO Aliphatic Aldehyde

1730 cm

-1

Wavenumbers, cm

-1

5001000150020002500300035004000

% Transmittance

020406080100

Figure IR-35. 5-Hexene-2-one, neat liquid: CH

2 =CH 2 CH 2 CH 2 COCH 3 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(CO 2 )R 1750-1735 S(sh) 33, 34 carboxylic acids RCO 2

H 1720-1680 S(sh) 26,27,30

amides (Amide I) RCONH 2 , RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH 2 1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR 2 1650-1620 S(sh) 23
anhydrides R(CO 2

CO)R 1820, 1750 S, S(sh) 36

carboxylates R(CO 2 ) - , M + 1600, 1400 S,S(sh) 42

C=C olefins R

2 C=CR 2 1680-1640 W(sh) 10, 39, 40
R 2 C=CH 2 1600-1675 M(sh) 9, 35
R 2

C=C(OR)R 1600-1630 S(sh) 41

-NO 2 nitro groups RNO 2 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

% Transmittance

020406080100

Top: CHCl

3 vs CHCl 3

Bottom: 2.5 % v/v un CHCl

3

Aliphatic Ester

Figure IR-33. Methyl acetate in 0.1 mm NaCl cells: CH 3 CO 2 CH 3 1720 cm
-1

Wavenumbers, cm

-1

5001000150020002500300035004000

% Transmittance

020406080100

Top: CHCl

3 vs CHCl 3

Bottom: 2.5 % v/v un CHCl

3 CCl 4 neat

1746 cm

-1

1748 cm

-1

1720 cm

-1 methyl acetate in different solvents

Wavenumber, cm

-1

1000150020002500300035004000

% Transmittance

020406080100120

liquid filmvapor: 106 °C Figure IR-34. Vapor and liquid spectra of ethyl n-hexanoate: CH 3 CH 2 CH 2 CH 2 CH 2 CO 2 CH 2 CH 3

Aliphatic Ester

The 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(CO 2 )R 1750-1735 S(sh) 33, 34 carboxylic acids RCO 2

H 1720-1680 S(sh) 26,27,30

amides (Amide I) RCONH 2 , RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH 2 1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR 2 1650-1620 S(sh) 23
anhydrides R(CO 2

CO)R 1820, 1750 S, S(sh) 36

carboxylates R(CO 2 ) - , M + 1600, 1400 S,S(sh) 42

C=C olefins R

2 C=CR 2 1680-1640 W(sh) 10, 39, 40
R 2 C=CH 2 1600-1675 M(sh) 9, 35
R 2

C=C(OR)R 1600-1630 S(sh) 41

-NO 2 nitro groups RNO 2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments.

R is an aliphatic group.

Aliphatic Acid

vapor 1740 cm -1 neat 1710 cm -1

Figure IR-26. The vapor,

liquid and CCl 4 soln spectra of hexanoic acid: CH 3 (CH 2 ) 4 CO 2 H

Wavenumber, cm

-1

1000150020002500300035004000

% Transmittance

020406080100120

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(CO 2 )R 1750-1735 S(sh) 33, 34 carboxylic acids RCO 2

H 1720-1680 S(sh) 26,27,30

amides (Amide I) RCONH 2 , RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH 2 1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR 2 1650-1620 S(sh) 23
anhydrides R(CO 2

CO)R 1820, 1750 S, S(sh) 36

carboxylates R(CO 2 ) - , M + 1600, 1400 S,S(sh) 42

C=C olefins R

2 C=CR 2 1680-1640 W(sh) 10, 39, 40
R 2 C=CH 2 1600-1675 M(sh) 9, 35
R 2

C=C(OR)R 1600-1630 S(sh) 41

-NO 2 nitro groups RNO 2 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

% Transmittance

102030405060708090100

Amide IAmide II

Figure IR-21. N-Methyl acetamide, neat liquid; thin film: CH 3

CONHCH

3 Secondary Amide

1650 cm

- 1

1550 cm

- 1

Wavenumbers, cm

-1

5001000150020002500300035004000

% Transmittance

020406080100

Figure IR-23. N,N-Dimethylacetamide, neat liquid; thin film: CH 3

CON(CH

3 ) 2 Tertiary Amide

No amide II band

1550 cm

- 1

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(CO 2 )R 1750-1735 S(sh) 33, 34 carboxylic acids RCO 2

H 1720-1680 S(sh) 26,27,30

amides (Amide I) RCONH 2 , RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH 2 1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR 2 1650-1620 S(sh) 23
anhydrides R(CO 2

CO)R 1820, 1750 S, S(sh) 36

carboxylates R(CO 2 ) - , M + 1600, 1400 S,S(sh) 42

C=C olefins R

2 C=CR 2 1680-1640 W(sh) 10, 39, 40
R 2 C=CH 2 1600-1675 M(sh) 9, 35
R 2

C=C(OR)R 1600-1630 S(sh) 41

-NO 2 nitro groups RNO 2 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

% Transmittance

020406080100

Figure IR-36. Propionic anhydride, neat liquid: CH 3 CH 2 CO 2 COCH 2 CH 3 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(CO 2 )R 1750-1735 S(sh) 33, 34 carboxylic acids RCO 2

H 1720-1680 S(sh) 26,27,30

amides (Amide I) RCONH 2 , RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH 2 1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR 2 1650-1620 S(sh) 23
anhydrides R(CO 2

CO)R 1820, 1750 S, S(sh) 36

carboxylates R(CO 2 ) - , M + 1600, 1400 S,S(sh) 42

C=C olefins R

2 C=CR 2 1680-1640 W(sh) 10, 39, 40
R 2 C=CH 2 1600-1675 M(sh) 9, 35
R 2

C=C(OR)R 1600-1630 S(sh) 41

-NO 2 nitro groups RNO 2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments.

R is an aliphatic group.

1410 cm

-1

1560 cm

-1

1560 cm

- 1

1400 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(CO 2 )R 1750-1735 S(sh) 33, 34 carboxylic acids RCO 2

H 1720-1680 S(sh) 26,27,30

amides (Amide I) RCONH 2 , RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH 2 1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR 2 1650-1620 S(sh) 23
anhydrides R(CO 2

CO)R 1820, 1750 S, S(sh) 36

carboxylates R(CO 2 ) - , M + 1600, 1400 S,S(sh) 42

C=C olefins R

2 C=CR 2 1680-1640 W(sh) 10, 39, 40
R 2 C=CH 2 1600-1675 M(sh) 9, 35
R 2

C=C(OR)R 1600-1630 S(sh) 41

-NO 2 nitro groups RNO 2 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

% Transmittance

020406080100

HC=C stretches CH 3 ,CH 2 symmetric and asymmetric stretchesC=C stretch CH 3 ,CH 2 bending vibrations(CH2) 4 rocking out of plane

H wag of vinyl

group 900, 1000 cm -1 ) Figure IR-9. 1-Heptene; neat sample, thin film: H 2 C=CH -CH 2 CH 2 CH 2 CH 2 CH 3

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(CO 2 )R 1750-1735 S(sh) 33, 34 carboxylic acids RCO 2

H 1720-1680 S(sh) 26,27,30

amides (Amide I) RCONH 2 , RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH 2 1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR 2 1650-1620 S(sh) 23
anhydrides R(CO 2

CO)R 1820, 1750 S, S(sh) 36

carboxylates R(CO 2 ) - , M + 1600, 1400 S,S(sh) 42

C=C olefins R

2 C=CR 2 1680-1640 W(sh) 10, 39, 40
R 2 C=CH 2 1600-1675 M(sh) 9, 35
R 2

C=C(OR)R 1600-1630 S(sh) 41

-NO 2 nitro groups RNO 2 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

% Transmittance

020406080100

Figure IR-40. 2,5-Dimethoxy2,5-dihydrofuran, neat liquid: OOCH 3 CH 3 O

Wavenumbers, cm

-1

5001000150020002500300035004000

% Transmittance

020406080100

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 NO

2 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(CO 2 )R 1750-1735 S(sh) 33, 34 carboxylic acids RCO 2

H 1720-1680 S(sh) 26,27,30

amides (Amide I) RCONH 2 , RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH 2 1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR 2 1650-1620 S(sh) 23
anhydrides R(CO 2

CO)R 1820, 1750 S, S(sh) 36

carboxylates R(CO 2 ) - , M + 1600, 1400 S,S(sh) 42

C=C olefins R

2 C=CR 2 1680-1640 W(sh) 10, 39, 40
R 2 C=CH 2 1600-1675 M(sh) 9, 35
R 2

C=C(OR)R 1600-1630 S(sh) 41

-NO 2 nitro groups RNO 2 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

% Transmittance

020406080100120

symmetric and asymmetric -NO 2 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

% Transmittance

020406080100

carbon-carbon triple bond stretch H

Wavenumbers, cm

-1

5001000150020002500300035004000

% Transmittance

2030405060708090

overtones of the benzene ring

Benzene, neat, thin film:


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