The hydrolytic reactivity of β-sultams

Nicholas J. Baxter, Andrew P. Laws, Laurent Rigoreau, Michael I. Page

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

N-Methyl β-sultam undergoes acid- and base-catalysed hydrolysis in water at 30 °C and I = 1.0 mol dm-3 with kH+ = 2.79dm3 mol-1s-1 and KOH = 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.

Original languageEnglish
Article number6/05903A
Pages (from-to)2245-2246
Number of pages2
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number11
DOIs
Publication statusPublished - 1996

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