Amine: An Organic Nitrogen Compound

Amine - a substituted ammonia molecule with basic properties. ( a derivative of

ammonia, in which one or more H atoms have been replaced by an alkyl
group.)

an organic compounds which contain and based on one or more atoms of

nitrogen.
a derivative of ammonia, in which one or more H atoms have been replaced by
an alkyl group.
with the general formula RNH2, R2NH or R3N

Classifications
1. Primary (1o) when one of three H atoms in ammonia is replaced by an alkyl
group.
2

CH3

2. Secondary (2o) when two of H atoms is replaced.

3. Tertiary (3o) when all of the H atoms are replaced by a substituent.

CH CH

CH3

CH2CH3
CH3

CH3CH2
Examples:
2.
3.

CH3CH2CH2NH2
CH3CH2NCH2CH3
CH3CH2CH2NCH2CH2CH3
CH3CH2CH2CH3

1.

4.
5.
6.

CH3NCH2
CH3CH2CH2CH2CH2NCH2CH2CH3

7.

8.
Naming
A. Primary amines( R-NH2)
- can be named by replacing the e of the parent group with amine.
- NH2 group can also be named as substituent using the group name, amino.
9. Examples:
NH2

10.

2.
3.
4.

CH3CHCH3
CH3CH2NH2
CH3CH2CH2NH2
CH3CH2CHCH2
NH2
NH2

1.

11.

5. CH3CH2CH2CH2CH2NH2
6. CH3CH2CHCH2CH3
7. CH3CH2CHCH2CH2CH3
12.

2-propanamine
ethanamine
propanamine
2-butanamine

2-aminopropane
aminoethane
aminopropane
2-aminobutane

pentanamine
3-pentanamine
4-hexanamine

aminopentane
3-aminopentane
4-aminohexane

CH3
NH
2

8. CH3CH2CCH3
13.

2-methyl 2-butanamine

2-methyl 2-butanamine

NH2

14.

9. CH3CHCHCH2CH2CH3 4-methyl 5-hexanamine 4-methyl 5-aminohexane

15.
10. CH3CH2CH2CHCH2CH2CH2CH3
4-methyl 2-heptanamine 4-methyl 2-aminoheptane
16.
a. Diamines
The final e is not omitted.
NH2

CH3

NH2

17.

1,2-ethanediamine
1,3-propanediamine
1,6-hexanediamine
2,4-pentanediamine

CH3

16. CH3CHCH2CH2CHCHCHCHCH3
CH3 NH2

CH2CH3

21.

1,2-diaminoethane
1,3-diaminopropane
1,6-diaminohexane
2,4-diaminopentane

5-ethyl 7-methyl 2,3-octadiamine 5-ethyl 7-methyl 2,3-diamineoctane

CH NH
2
3
NH2
CH2CH3

20.

NH2

19.

NH2

15.

H2N--CH2CH2--NH2
H2N--CH2CH2CH2--NH2
H2N(CH2)6NH2
CH3CHCH2CHCH3
18.
CH3CHCH2CH2CH2CHCHCH3
NH2

11.
12.
13.
14.

8-ethyl 2,3-dimethyl 4,5-nonadiene/ diaminenonane

b. Primary Cyclo-amines
17.
Cyclopentanamine
22.

aminocyclopentane

NH2

23.

18. `
Cyclohexanamine
aminocyclohexane
24.
B. Secondary Amines (R2NH)
- Named as N-substituted primary amines by using the longest continuous
NH2

carbon chain as the parent name.

N represents the alkyl groups attached to the nitrogen atom.

25. Examples:
19. CH3NHCH2CH2CH3
20. CH3CH2NHCH2CH2CH2CH3

N-methyl-1-propanamine
N-ethyl-1-butanamine

21. NHCH2CH2CH2CH2CH2CH3
N-propyl-1-hexanamine
26.
22. CH3CH2CH2CH2CH2NHCH2CH3
N-pentyl-1-ethanamine
23. CH3CH2CH2CH2NHCH2CH2CH2CH2CH3
N-butyl-1-pentanamine
24. CH3CHCH2NHCH2CH2CH2CH3
N-2-methylpropyl-1-butanamine
27.
25. CH3CH2CHCH2CH2NHCH2CH2CH2CH3
N-3-ethylpentyl-1-butanamine
28.
26. CH3CH2CH2NHCH2CHCH2CH3
N-propyl-2-methyl-1-butanamine
29.
C. Tertiary Amines (R3N)
- named in a manner like secondary amines, wherein N is used as a
CH2CH2CH3
CH3

CH2CH3

CH3

substitute to the alkyl groups attached to the nitrogen atom.

30. Examples
27. CH3NCH2CH2CH2CH3

N,N-dimethyl-1-butanamine

CH3

31.

28. CH3CH2NCH2CH2CH2CH2CH3
32.
29. CH3NCH2CH2CH2CH3
33.
30. CH3CH2CH2NCH2CH3
34.
31. CH3NCH2CH2CHCH2CH2CH3

N,N-diethyl-1-pentanamine
N-ethyl-N-methyl-1-butanamine

CH2CH3

N-ethyl-N-propyl-1-ethanamine

CH2CH3

CH2CH3

CH2CH3

CH3

35.

N,N-dimethyl-3-methyl-1-hexanamine

CH3

32. CH3CH2NCH2CH2CH2CHCHCH2CH3

CH2CH3

CH2CH3

CH3CH2CH2NCH2CHCH2CHCHCH3
CH3

CH3

CH3

CH2CH3

38.

CH3CH2NCH2CHCH2CHCH2CHCHCH3
CH3

40.

CH3

39.

N-ethyl-N-propyl-2,4,5-trimethyl-1-hexanamide
N-ethyl-N-methyl-2,4,6,7-tetramethyl-1-octanamine

CH3 CH3

35.

N-ethyl-N-methyl-4-ethyl-1-pentanamide

CH3

CH3NCH2CH2CH2CHCH3

37.
34.

CH2CH3

33.

N,N-diethyl-4,5-diethyl-heptanamine

CH2CH3

36.

Another way of naming amines is through their common names. Some

simple amines are most often referred to by their common names. The names for
aliphatic amines are formed by naming the alkyl group attached to the nitrogen atom,
followed by the ending amine.
41.
is propylamine

CH3 is methyl; CH3NH2 is methylamine

CH3CH2CH2 is propyl; CH3CH2CH2NH2

42.

C2H6 is ethyl; C2H6NH2 is ethylamine

43.

(CH3)2 is dimethyl; (CH3)2NH is dimethylamine

44.

(CH3)3 is trimethyl; (CH3)3 is trimethylamine

45.

Aromatic Amines

46.

The most important aromatic amines is aniline. (C 6H5NH2).

Derivatives are named as substituted anilines. To identify a substituted aniline in which

the alkyl group is attached to the nitrogen atom, an N- is placed before the group name
to indicate that it is bonded to nitrogen atom and not to the carbon atom in the ring.
47. Examples
CH3
NHCH

CH
NH2CH
3
2

aniline

49.

CH3

48.

N-ethyl-N-methylaniline
N,N-dimethylaniline

50.
N-methylaniline

51.

CH2CH3
CH3
CH2CH3

N-methyl-N-butylaniline
N,N-diethylaniline
N
CH2CH2CH3
CH2CH3

53.

CH2CH2CH2CH3

52.

54.
55.
N-ethyl-N-propylaniline

56.
57.

When a group is substituted for an H atom in the ring, the resulting ringsubstituted aniline is named as previously done with aromatic compounds.
Toluidines monomethyl ring-substituted amines.

58.

NH2

CH3

CH2CH3

62.

(p-methylaniline) (m-methylaniline) (o-methylaniline)

NH2
m-toluidine

NH2
o-toluidine

CH3

CH3

CH3

CH3

64.

NH2
p-toluidine

63.

N-ethylaniline

CH3

61.

CH3

60.

m-ethylaniline

NH2

NH2

HNCH2CH3

59.

NH2

65.

p-chlooaniline

2,3-dimethylaniline
68.

2,3,4-trimethylaniline

Cl

67.

CH3

66.

69.
70.
Physiologically, aniline is a toxic substance. It is easily absorbed
through the skin and affects both the blood and the nevous system. Aniline
reduces the oxygen-carrying capacity of the blood by converting hemoglobin to
methemoglobin. Methemoglobin is the oxidized form of hemoglobin in which the
iron has gone from a +2 to a +3 oxidation state.
71.
72.

Heterocyclic Compounds ring compounds in which the atoms in the ring are
not all alike.

The most common heteroatoms are oxygen, nitrogen and sulfur. A number
of the nitrogen-containing heterocyclic compounds are present in naturally
occurring biological substances such as DNA, which controls heredity.
N

73.

74. Examples:
N

75.

NN

77.

82.
83.

Pyridine
(C5H5N)

81.

Piperidine
(C5H11N)

80.

Pyrimidine
(C4H4N2)

Pyrrole
(C4H5N)
H
H
79.

Purine
(C5H4N4)

78.

76.

Some aromatic amines are all liquids or solids. They are colorless or
almost colorless when freshly prepared, but become dark brown when exposed
to air and light.