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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
Metadata only available from this repository.Official URL: http://dx.doi.org/10.1039/P29910001213
DOI: 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 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 |
| Related URLs: | |
| Depositing User: | Sharon Beastall |
| Date Deposited: | 06 Nov 2009 09:51 |
| Last Modified: | 06 Nov 2009 09:51 |
| URI: | http://eprints.hud.ac.uk/id/eprint/6116 |
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