The hydrolytic reactivity of β-sultams

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

doi:10.1039/P29960002245

The hydrolytic reactivity of β-sultams

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

Research output: Contribution to journal › Article › peer-review

32 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 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.

Original language	English
Article number	6/05903A
Pages (from-to)	2245-2246
Number of pages	2
Journal	Journal of the Chemical Society. Perkin Transactions 2
Issue number	11
DOIs	https://doi.org/10.1039/P29960002245
Publication status	Published - 1996

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title = "The hydrolytic reactivity of β-sultams",

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.",

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T1 - The hydrolytic reactivity of β-sultams

AU - Baxter, Nicholas J.

AU - Laws, Andrew P.

AU - Rigoreau, Laurent

AU - Page, Michael I.

PY - 1996

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N2 - 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.

AB - 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.

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The hydrolytic reactivity of β-sultams

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