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The mechanisms of hydrolysis of the ?-lactam isatin and its derivatives

Casey, Lorraine A., Galt, Ronald H. B. and Page, Michael I. (1993) The mechanisms of hydrolysis of the ?-lactam isatin and its derivatives. Journal of the Chemical Society, Perkin Transactions 2 (1). pp. 23-28. ISSN 1472-779X

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Abstract

The pH dependences of the rates of hydrolysis of isatin, its N-carboxymethyl derivative and its 5-nitro substituted analogues exhibit a complex behaviour, showing a first- and second-order dependence upon hydroxide ion concentration, as well as a pH-independent pathway. The pH dependence is interpreted in terms of the formation of tetrahedral intermediates in different protonic states which may break down to products via hydroxide ion, hydronium ion and water catalysed pathways. These -lactams are as reactive, or more reactive, than benzylpenicillin.

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 08:39
Last Modified: 06 Nov 2009 08:39
URI: http://eprints.hud.ac.uk/id/eprint/6110

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