Hydrolysis of peptide bonds : participation of a carboxyl group in amide hydrolysis

摘要

In order to assess the effect of substituents on the participation of a neighbouring carboxyl group in the hydrolysis of amides, seventeen substituted succinamic acids have been prepared. Their rates of hydrolysis have been determined at three temperatures, and their rates and thermodynamic functions have been correlated at 70°. The mechanism of the hydrolysis has been discussed and the effect of the substituents interpreted in terms of their bulk and electronic characters.