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

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

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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.

Original languageEnglish
Pages (from-to)298-299
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number6
Publication statusPublished - 1 Dec 1979


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