The hydrolytic reactivity of β-sultams

Article abstract of DOI:10.1039/P29960002245

N-Methyl β-sultam undergoes acid- and base-catalysed hydrolysis in water at 30 °C and I = 1.0 mol dm^-3 with k^H+ = 2.79dm³ mol^-1s^-1 and K^OH = 1.38 × 10^-2 dm³ mol^-1 s^-1. These second-order rate constants are approximately 10⁹ and 10⁷, respectively, greater than those for a similar acyclic sulfonamide. The entropy of activation for the acid-catalysed hydrolysis of the β-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.

Full text of DOI:10.1039/P29960002245

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online