Phenylureas. Part 2. Mechanism of the acid hydrolysis of phenylureas

Abstract

The mechanism of the hydrolytic decomposition of phenylureas in acid media is investigated. It includes, in part, knowledge already present in the literature. Over the investigated pH range the occurrence of a rate maximum in the pH curves due to the strongly reduced water activity at higher acid strengths is observed. An addition–elimination mechanism with rate-determining attack of water at the N-protonated substrate is proposed. The reversion of the substituent influence on the reaction rate with increasing acidity of the reaction medium points to a change of the hydrolytic decomposition mechanism in strongly acidic media.