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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
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

Information
URI:
https://eprints.hud.ac.uk/id/eprint/6174
URI:
https://eprints.hud.ac.uk/id/eprint/6174
URI:
https://eprints.hud.ac.uk/id/eprint/6174
URI:
https://eprints.hud.ac.uk/id/eprint/6174
URI:
https://eprints.hud.ac.uk/id/eprint/6174
URI:
https://eprints.hud.ac.uk/id/eprint/6174
Title:
Intramolecular general acid catalysis in the aminolysis of benzylpenicillin. A preferred direction of nucleophilic attack
Creators:
Martin, Anthony F., Morris, Jeffrey J. and Page, Michael I.
Identification Number:
10.1039/C39790000298
Official URL:
http://dx.doi.org/10.1039/C39790000298
Date:
March 1979
Subjects:
Q Science > Q Science (General)
Q Science > QD Chemistry
Schools:
School of Applied Sciences
Library
Item Type:
Article
Depositing User:
Sharon Beastall
Date Deposited:
11 Nov 2009 12:42
Revision:
11
Last Modified:
28 Aug 2021 10:52
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