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Nitrogen Compounds
Why are amides, RCONH2, less basic than amines, RNH2?
Amides form a zwitterion in which the nitrogen atom carries a positive charge
Amides have a resonance structure involving the movement of a pair of electrons from the nitrogen atom to the oxygen atom
Electrons on the nitrogen atom move on to the C-N bond giving it some double bond character so that it is more difficult to break
The amide carbonyl group withdraws electrons from the NH2 group to make the hydrogen atoms acidic
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Explanation
The lone pair of electrons on N is involved in delocalization. Hence it is less available for protonation, i.e. it is less basic compared to an amine.
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