Alcohol-catalysed Hydrolysis of Benzylpenicillin

Andrew M. Davis, Philip Proctor, Michael I. Page

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

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 Brønsted 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.

LanguageEnglish
Pages1213-1217
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number8
DOIs
Publication statusPublished - Aug 1991

Fingerprint

Penicillin G
beta-Lactams
Hydrolysis
Alcohols
Ions
Trifluoroethanol
Protonation
Isotopes
Penicillins
Catalysis
Esters
Nitrogen
Oxygen
Water

Cite this

Davis, Andrew M. ; Proctor, Philip ; Page, Michael I. / Alcohol-catalysed Hydrolysis of Benzylpenicillin. In: Journal of the Chemical Society, Perkin Transactions 2. 1991 ; No. 8. pp. 1213-1217.
@article{7c83b6b278b2452bb0388c05b4fe3614,
title = "Alcohol-catalysed Hydrolysis of Benzylpenicillin",
abstract = "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 Br{\o}nsted 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.",
author = "Davis, {Andrew M.} and Philip Proctor and Page, {Michael I.}",
year = "1991",
month = "8",
doi = "10.1039/P29910001213",
language = "English",
pages = "1213--1217",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
issn = "0300-922X",
publisher = "Chemical Society",
number = "8",

}

Alcohol-catalysed Hydrolysis of Benzylpenicillin. / Davis, Andrew M.; Proctor, Philip; Page, Michael I.

In: Journal of the Chemical Society, Perkin Transactions 2, No. 8, 08.1991, p. 1213-1217.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Alcohol-catalysed Hydrolysis of Benzylpenicillin

AU - Davis, Andrew M.

AU - Proctor, Philip

AU - Page, Michael I.

PY - 1991/8

Y1 - 1991/8

N2 - 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 Brønsted 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.

AB - 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 Brønsted 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.

UR - http://www.scopus.com/inward/record.url?scp=37049086897&partnerID=8YFLogxK

U2 - 10.1039/P29910001213

DO - 10.1039/P29910001213

M3 - Article

SP - 1213

EP - 1217

JO - Journal of the Chemical Society, Perkin Transactions 2

T2 - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

SN - 0300-922X

IS - 8

ER -