Intramolecular general acid catalysis in the aminolysis of benzylpenicillin. A preferred direction of nucleophilic attack

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Martin, Anthony F., Morris, Jeffrey J. and Page, Michael I. (1979) Intramolecular general acid catalysis in the aminolysis of benzylpenicillin. A preferred direction of nucleophilic attack. Chemical Communications (6). pp. 298-299. ISSN 1359-7345

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Official URL: http://dx.doi.org/10.1039/C39790000298

DOI: 10.1039/C39790000298

Abstract

The reaction of 1,2-diaminoethane monocation with benzylpenicillin shows a rate enhancement of ca. 100-fold compared with a monoamine of similar basicity; this is attributed to intramolecular general acid catalysis which in turn indicates that nucleophilic attack takes place from the least hindered -side in disagreement with the prediction of the theory of stereoelectronic control

Item Type:	Article
Subjects:	Q Science > Q Science (General) Q Science > QD Chemistry
Schools:	School of Applied Sciences
Related URLs:	Author
Depositing User:	Sharon Beastall
Date Deposited:	11 Nov 2009 12:42
Last Modified:	11 Nov 2009 12:42
URI:	http://eprints.hud.ac.uk/id/eprint/6174

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