The imidazole-catalysed isomerisation of benzylpenicillin
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 7,p. 827-831
- https://doi.org/10.1039/p29820000827
Abstract
The isomerisation of benzylpenicillin to benzylpenicillenic acid is catalysed by imidazole, N-methylimidazole, and 2-methylimidazole. For each catalyst there is a different rate equation. The dominant reaction path is general acid assisted reaction of benzylpenicillin with imidazole. A mechanism is proposed in which, after reaction with the imidazole at the carbonyl group of the β-lactam ring, there is protonation of the β-lactam nitrogen and ring-opening. The mechanism proposed parallels that suggested by Morris and Page for the aminolysis of penicillins.Keywords
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