Kinetic and mechanistic studies of the hydrolysis of sulfamate esters: a non-elimination decomposition route

The kinetics of hydrolysis at pH 2 and ionic strength (μ) = 1 of a series of sulfamate esters p-XC6H4OSO2NH2 have been examined using structure- and solvent-reactivity studies, thermodynamic data, a ‘nucleophilicity test’ and a kinetic solvent isotope effect to probe the mechanism of the hydrolysis. These esters can be regarded as models for the more complex medicinally and biologically important esters now under extensive study. The mechanism of hydrolysis involves the neutral ester undergoing nucleophilic attack by water in a bimolecular TS.