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January 1, 1991Journal of the Chemical Society Perkin Transactions 2

Alcohol-catalysed hydrolysis of benzylpenicillin

A. M. Davis Philip Proctor Michael I. Page

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Abstract

The hydrolysis of benzylpenicillin is catalysed by alkoxide ions and other oxygen bases. Catalysis occurs by a nucleophilic pathway and the intermediate ester can be detected in some cases. The Brønsted βnuc for alkoxide ions is 0.97, and is compatible with rate-limiting ring opening of the β-lactam. A solvent isotope effect of 3.2 for the trifluoroethanol-catalysed reaction suggests protonation by water occurs to the departing β-lactam nitrogen. Penicillin is not a particularly effective acylating agent of alcohols.

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Davis et al. (1991) studied this question.

synapsesocial.com/papers/6a82d625d88fdfcf4fa0cea7 https://doi.org/10.1039/p29910001213

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