The Mechanisms of Hydrolysis of the y-Lactam lsatin and its Derivatives

Lorraine A. Casey, Ron Galt, Michael I. Page

Research output: Contribution to journalArticle

26 Citations (Scopus)

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 γ-lactams are as reactive, or more reactive, than benzylpenicillin.

LanguageEnglish
Pages23-28
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number1
DOIs
Publication statusPublished - 1 Jan 1993

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Lactams
Hydrolysis
Isatin
Derivatives
Penicillin G
Water
hydroxide ion
hydronium ion

Cite this

Casey, Lorraine A. ; Galt, Ron ; Page, Michael I. / The Mechanisms of Hydrolysis of the y-Lactam lsatin and its Derivatives. In: Journal of the Chemical Society, Perkin Transactions 2. 1993 ; No. 1. pp. 23-28.
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The Mechanisms of Hydrolysis of the y-Lactam lsatin and its Derivatives. / Casey, Lorraine A.; Galt, Ron; Page, Michael I.

In: Journal of the Chemical Society, Perkin Transactions 2, No. 1, 01.01.1993, p. 23-28.

Research output: Contribution to journalArticle

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