A nitrogen isotope effect study of an aromatic nucleophilic substitution reaction
Abstract
Hydrolysis of p-nitroaniline in aqueous sodium hydroxide was found to be second order with an activation energy of 17 kcal./mole and an entropy of activation of ca.–33 e.u. Absence of a significant nitrogen isotope effect for the reaction established that C–N bond stretching was unimportant in the rate-determining transition state.