ALCOHOL-CATALYZED HYDROLYSIS OF BENZYLPENICILLIN

被引：30

作者：

DAVIS, AM ^{[1
]}

PROCTOR, P ^{[1
]}

PAGE, MI ^{[1
]}

机构：

[1] HUDDERSFIELD POLYTECH,DEPT CHEM & PHYS SCI,HUDDERSFIELD HD1 3DH,W YORKSHIRE,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1991年 / 08期

关键词：

D O I：

10.1039/p29910001213

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 beta-nuc for alkoxide ions is 0.97, and is compatible with rate-limiting ring opening of the beta-lactam. A solvent isotope effect of 3.2 for the trifluoroethanol-catalysed reaction suggests protonation by water occurs to the departing beta-lactam nitrogen. Penicillin is not a particularly effective acylating agent of alcohols.

引用

页码：1213 / 1217

页数：5

共 37 条

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