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

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

Research output: Contribution to journalArticle

18 Citations (Scopus)

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.

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

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ethylenediamine
Penicillin G
Alkalinity
Catalysis
Acids
Direction compound

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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 α-side in disagreement with the prediction of the theory of stereoelectronic control.",
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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.; Page, Michael I.

In: Journal of the Chemical Society, Chemical Communications, No. 6, 01.12.1979, p. 298-299.

Research output: Contribution to journalArticle

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