Search:
Computing and Library Services - delivering an inspiring information environment

Intra- and inter-molecular catalysis in the aminolysis of benzylpenicillin

Morris, Jeffrey J. and Page, Michael I. (1980) Intra- and inter-molecular catalysis in the aminolysis of benzylpenicillin. Journal of the Chemical Society, Perkin Transactions 2 (1). pp. 212-219. ISSN 1472-779X

Metadata only available from this repository.

Abstract

The rate law for the aminolysis of benzylpenicillin in water is reported. The Brønsted -values for the uncatalysed, the amine-catalysed, and hydroxide-ion catalysed reactions are 1.0, 1.09, and 0.96 respectively. This indicates that in the transition states for all three pathways the amine nucleophile contains a unit positive charge which is consistent with the formation of a tetrahedral intermediate. Intramolecular general base catalysis occurs with the reaction of ethylenediamine and, despite the importance of general base catalysis in the aminolysis reaction, the effective concentration of the catalysing base is only ca. 1M, which is attributed to the loose transition state involved in intermolecular catalysis. Intramolecular general acid catalysis occurs with the reaction of ethylenediamine monocation. This suggests that nucleophilic attack takes place from the least hindered -side.

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 08:26
Last Modified: 12 Nov 2009 08:26
URI: http://eprints.hud.ac.uk/id/eprint/6190

Item control for Repository Staff only:

View Item

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