Alcohol-catalysed hydrolysis of benzylpenicillin
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 8,p. 1213-1217
- https://doi.org/10.1039/p29910001213
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.Keywords
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