amide vs amine basicity

Question

Amides are far less basic than amines because:

RankGuru · Accepted Answer

1. **Amine Basicity**: In an amine ($R-NH_2$), the lone pair on Nitrogen is localized and available for donation.
2. **Amide Structure**: In an amide ($R-CO-NH_2$), the Nitrogen atom is adjacent to a carbonyl group ($C=O$).
3. **Resonance**: The lone pair on Nitrogen can be delocalized through resonance into the Oxygen atom ($N^+ = C - O^-$).
4. **Consequence**: This **resonance delocalization** significantly reduces the electron density on the Nitrogen atom.
5. **Basicity**: As a result, amides are very weak bases; in fact, they behave as amphoteric substances or very weak acids in certain conditions.

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amide vs amine basicity

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