Ab initio calculations on neutral and alkaline hydrolyses of beta-lactam antibiotics. A theoretical study including solvent effects

被引：59

作者：

Pitarch, J

RuizLopez, MF

PascualAhuir, JL

Silla, E

Tunon, I

机构：

[1] UNIV NANCY 1, CHIM THEOR LAB, URA CNRS 510, F-54506 VANDOEUVRE LES NANCY, FRANCE

[2] UNIV VALENCIA, DEPT QUIM FIS, E-46100 BURJASSOT, VALENCIA, SPAIN

来源：

JOURNAL OF PHYSICAL CHEMISTRY B | 1997年 / 101卷 / 18期

关键词：

D O I：

10.1021/jp963387u

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

In this work we present a theoretical study of neutral and alkaline hydrolyses of N-methylazetidinone as a model of biological hydrolysis of beta-lactam antibiotics. Calculations have been carried out at the HF and MP2 levels using the 3-21G, 6-31G*, and 6-31+G* basis sets. Solvent effects have been included by means of a polarizable continuum model. Our results indicate two possible reaction mechanisms for the beta-lactam hydrolysis: concerted and stepwise. In both the neutral and alkaline hydrolyses the concerted mechanism presents a free energy barrier lower than that of the stepwise mechanism.

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页码：3581 / 3588

页数：8

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