Alcohol-catalysed hydrolysis of benzylpenicillin

Andrew M. Davis; Philip Proctor; Michael I. Page

doi:10.1039/P29910001213

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Journal of the Chemical Society, Perkin Transactions 2

Issue 8, 1991

Perkin Transactions 2 ceased publication in 2002. Organic & Biomolecular Chemistry is the RSC's organic chemistry journal for high-quality, original organic chemistry research.

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Alcohol-catalysed hydrolysis of benzylpenicillin

Andrew M. Davis, Philip Proctor and Michael I. Page

J. Chem. Soc., Perkin Trans. 2, 1991, 1213-1217

DOI: 10.1039/P29910001213

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Abstract
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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 β_nuc 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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Journal of the Chemical Society, Perkin Transactions 2

Alcohol-catalysed hydrolysis of benzylpenicillin

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