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

Fingerprint Dive into the research topics of 'Intramolecular general acid catalysis in the aminolysis of benzylpenicillin. A preferred direction of nucleophilic attack'. Together they form a unique fingerprint.

  • Cite this