Water-assisted alkaline hydrolysis of monobactams:: A theoretical study

被引：0

作者：

Díaz, N

Suárez, D

Sordo, TL

Tuñón, I

Silla, E

机构：

[1] Univ Oviedo, Dept Quim Fis & Analit, E-33006 Oviedo, Spain

[2] Univ Valencia, Dept Quim Fis, E-46100 Valencia, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2002年 / 8卷 / 04期

关键词：

alkaline hydrolysis; density functional calculations; monobactams; solvent effects; substituent effects;

D O I：

10.1002/1521-3765(20020215)8:4<859::AID-CHEM859>3.0.CO;2-I

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A theoretical study of the water-assisted alkaline hydrolysis of 2-azetidi-, none, 3-formylamino-2-azetidinone and 3-formylamino-2-azetidine-1-sulfonate ion is carried out at the B3LYP/6-31+G* level. The effect of bulk solvent is taken into account using the PCM solvation model while specific solvent effects are represented by the inclusion of an ancillary water molecule along the reaction profile. The calculated free energy barriers in solution are in reasonable agreement with experimental values. The observed substituent effects due to the presence of the 3-formylamino and the SO3 groups attached to the beta-lactam ring are crucial factors determining the hydrolysis of monobactam antibiotics.

引用

页码：859 / 867

页数：9

共 45 条

[1] A new definition of cavities for the computation of solvation free energies by the polarizable continuum model [J].