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

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 acid-catalysed hydrolysis is postulated as involving two steps: a rapid protonation and a rate-determining A-2 nucleophilic attack by water.