Computing and Library Services - delivering an inspiring information environment

Metal ion catalysis in the aminolysis of penicillin

Gensmantel, Nigel P., Gowling, Eric W. and Page, Michael I. (1978) Metal ion catalysis in the aminolysis of penicillin. Journal of the Chemical Society, Perkin Transactions 2 (4). pp. 335-342. ISSN 1472-779X

Metadata only available from this repository.


The copper(II) ion catalysed hydrolysis and aminolysis of benzylpenicillin in water at 30° shows saturation kinetics. A 1 : 1 complex is formed between the metal ion and benzylpenicillin which is attacked by hydroxide ion and amine ca. 107-fold faster than unco-ordinated benzylpenicilin. The Brønsted value for nucleophilic attack by amines is 0.87. The copper(II)ion catalysed reactions of the methyl ester of benzylpenicillin show much smaller rate enhancements indicating that the site of co-ordination for the antibiotic involves the ionised carboxy-group. The mechanism of the catalysed reactions does not involve the intermediate formation of benzylpenicillenic acid or a keten. The reactions are inhibited by buffers which co-ordinate to copper(II)ions. Trifluoroethylamine forms a 1 : 1 complex with copper(II) ion with an equilibrium constant of 15.6 l mol–1

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: 12 Nov 2009 08:41
Last Modified: 28 Aug 2021 10:52


Downloads per month over past year

Repository Staff Only: item control page

View Item View Item

University of Huddersfield, Queensgate, Huddersfield, HD1 3DH Copyright and Disclaimer All rights reserved ©