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

Martin, Anthony F.; Morris, Jeffrey J.; Page, Michael I.

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

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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: