Issue 6, 1979

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

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 α-side in disagreement with the prediction of the theory of stereoelectronic control.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1979, 298-299

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

A. F. Martin, J. J. Morris and M. I. Page, J. Chem. Soc., Chem. Commun., 1979, 298 DOI: 10.1039/C39790000298

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