Solvent effects on tautomerism equilibria in heterocycles

被引：62

作者：

Luque, FJ ^{[1
]}

LopezBes, JM ^{[1
]}

Cemeli, J ^{[1
]}

Aroztegui, M ^{[1
]}

Orozco, M ^{[1
]}

机构：

[1] UNIV BARCELONA,FAC FARM,DEPT FARM,E-08028 BARCELONA,SPAIN

来源：

THEORETICAL CHEMISTRY ACCOUNTS | 1997年 / 96卷 / 02期

关键词：

tautomeric equilibria; heterocycles; solvent effects; self-consistent reaction field; continuum electrostatics;

D O I：

10.1007/s002140050210

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：

High-level ab initio quantum mechanical used to analyze the tautomeric preferences in the gas phase and in aqueous solution of three important five-member heterocycles: 4-(5-)methylimidazole, 5-hydroxyisoxazole, and 3-hydroxypyrazole. Solvent effects have been introduced by means of self-consistent reaction field (SCRF) calculations at the ab initio level using our parametrized version of the polarizable continuum model developed by Miertus, Scrocco and Tomasi (MST), including geometry relaxation upon solvation. The extent to which the MST model, and SCRF methods in general, are suitable for the study of processes of this type is discussed.

引用

页码：105 / 113

页数：9

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