Alcohol-catalysed hydrolysis of benzylpenicillin

Autor:	Andrew M. Davis, Michael I. Page, Philip Proctor
Rok vydání:	1991
Předmět:	Acylation chemistry.chemical_compound Hydrolysis Reaction rate constant Nucleophile Chemistry Alkoxide polycyclic compounds Organic chemistry Protonation Alcohol Medicinal chemistry Catalysis
Zdroj:	Journal of the Chemical Society, Perkin Transactions 2. :1213
ISSN:	1364-5471 0300-9580
DOI:	10.1039/p29910001213
Popis:	The hydrolysis of benzylpenicillin is catalysed by alkoxide ions and other oxygen bases. Catalysis occurs by a nucleophilic pathway and the intermediate ester can be detected in some cases. The Bronsted βnuc for alkoxide ions is 0.97, and is compatible with rate-limiting ring opening of the β-lactam. A solvent isotope effect of 3.2 for the trifluoroethanol-catalysed reaction suggests protonation by water occurs to the departing β-lactam nitrogen. Penicillin is not a particularly effective acylating agent of alcohols.
Databáze:	OpenAIRE
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