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Home » Chemistry Homework Help » Organic Chemistsry » Amines Character
Amines Character
Amines act as Lewis bases due to the presence of a lone pair of electrons on nitrogen. They are stronger bases than water and are, therefore, protonated by water in their aqueous solution. The basic strength of amines are compared in terms of the equilibrium constant Kb, or pKb values are explained below from the equilibrium representing the protonation of amine by water.

Applying law of equilibrium



The product of two constants K × [H2O] is another constant Kb

RNH2 + H2O RNH3+ + OH-



The constant Kb is called basicity constant. A more convenient method of expressing the basic strength of amines is in terms of their pKb values (pKb = -log Kb). Each amine has its characteristic Kb or pKb. Now, larger the value of Kb or smaller the value of pKb, more is the basic strength of amine. The Kb and pKb values for some amines are given in the table below.

Compound Kb pKb
Ammonia, NH3 1.8 × 10-5 4.7
1˚ Amines    
Methylamine, CH3, NH2 4.5 × 10-4 3.38
Ethylamine, C2H5NH2 5.1 × 10-4 3.27
Propylamine, CH3(CH2)2NH2 4.1 × 10-4 3.39
2˚ Amines    
Dimethylamine, (CH3)2NH 5.4 × 10-4 3.29
Diethylamine, (C3H5)2NH 10 × 10-4 3
D-n-propylamine, (C3H7)2NH 10 × 10-4 3
3˚ Amines    
Trimethylamine, (CH3)3N 0.6 × 10-4 4.22
Triethylamine, (C2H5)3N 5.6 × 10-4 3.2
Tri-n-propylamine, (C3H7)3N 4.5 × 10-4 3.34

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