The hydrolytic reactivity of beta-sultams

N-Methyl beta-sultam undergoes acid- and base-catalysed hydrolysis in water at 30 degrees C and I = 1.0 mol dm(-3) with k(H+) = 2.79 dm(3)mol(-1)s(-1) and k(OH) = 1.38 x 10(-2) dm(3)mol(-1) s(-1), These second-order rate constants are approximately 10(9) and 10(7), respectively, greater than those for a similar acyclic sulfonamide. The entropy of activation for the acid-catalysed hydrolysis of the beta-sultam is -80 J K-1 mol(-1) which may be indicative of unimolecular ring opening, whereas that for the base-catalysed reaction, -184 J K-1 mol(-1), is consistent with a bimolecular process.