Ionization of Substituted Benzamides in Acid.

The acid-catalysed hydrolysis of amides has for a long time been assumed to involve a protonation of the amide in a fast preequilibrium step, followed by the rate-determing attack of a molecule of water on this protonated intermediate (1,2,3). Recently it has been shown that by taking account of the basic strength of the amide, many features of its hydrolysis might be explained; in particular, the fact that the rate of hydrolysis increases to a maximum and then decreases with increase in concentration of acid (4). [...