Investigation of the Acid-Catalyzed Hydrolysis and Reaction Mechanisms of N,N′-Diarylsulfamides Using Various Criteria

Abstract

The mechanism of acid-catalyzed hydrolysis of a series of p-substituted N,N′-diarylsulfamides was investigated in aqueous mineral acid solutions. Rate profiles, reaction activation parameters, catalytic order of strong acids, solvent isotope effects, and analysis of the kinetic data by the excess acidity method suggest a change in the mechanism from A2 to A1. While the hydrolysis proceeds with an A2 mechanism in low acidity regions, an A1 mechanism takes place in high acid concentrations. Copyright © 2013 John Wiley & Sons, Ltd.