Why are amides more resistant to hydrolysis than esters?
1 Answer
Mar 13, 2018
See Below
Explanation:
Amides have a significant resonance contribution from a form that gives the nitrogen a positive charge.
This image shows a peptide bond (amide bond), but the idea is the same. This resonance form reduces the stability of the Amine as a leaving group. The resonance form may also make the carbonyl carbon less polarized, and therefore less susceptible to nucleophilic attack.
