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Alcohol-catalysed hydrolysis of benzylpenicillin

Davis, Andrew M., Proctor, Philip and Page, Michael I. (1991) Alcohol-catalysed hydrolysis of benzylpenicillin. Journal of the Chemical Society, Perkin Transactions 2 (8). pp. 1213-1217. ISSN 1472-779X

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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 nuc for alkoxide ions is 0.97, and is compatible with rate-limiting ring opening of the -lactam. A solvent isotope effect of 3.2 for the trifluoroethanol-catalysed reaction suggests protonation by water occurs to the departing -lactam nitrogen. Penicillin is not a particularly effective acylating agent of alcohols

Item Type: Article
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Schools: School of Applied Sciences
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Depositing User: Sharon Beastall
Date Deposited: 06 Nov 2009 09:51
Last Modified: 28 Aug 2021 10:52


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