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

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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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
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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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