Kinetics and mechanism of the acid-catalysed hydrolysis of N-methyl-N-phenylsulphamate

Abstract

The catalytic effects of hydrochloric, perchloric, and sulphuric acids on the hydrolysis of N-methyl-N-phenylsulphamate salts have been examined and the data have been treated by the Bunnett and Bunnett–Olsen methods. Solvent isotope, salt, organic solvent, and temperature effects have also been probed. The mechanism of the acidcatalysed hydrolysis is postulated as involving two steps: a rapid, protonation and a rate-determining A-2 nucleophilic attack by water.