Studies on tautomeric stability and equilibrium of 5(4)-substituted-1,2,3 triazoles. I. Electronegativity and resonance effects of substituent

被引：4

作者：

Ramirez, Miguel A. ^{[1
,2
]}

Martin, V. S. ^{[1
,2
]}

Gallardo, Ana G. ^{[2
]}

机构：

[1] Univ La Laguna, Inst Univ Bioorgan Antonio Gonzalez, Tenerife 38206, Spain

[2] Univ La Laguna, Dept Quim Organ, Tenerife 38206, Spain

来源：

COMPUTATIONAL AND THEORETICAL CHEMISTRY | 2013年 / 1026卷

关键词：

1,2,3-Triazol; Tautomerism; NBO analysis; AIM charges; Group electronegativity; Resonance; SYSTEMS; 1,2,3-TRIAZOLES; HETEROCYCLES; DERIVATIVES; MODELS;

D O I：

10.1016/j.comptc.2013.10.008

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：

We have studied the 1,2,3-triazole system with a set of 25 substituents of different electronic features using several methods. Our aim is to find out a calculation method for the analysis of these molecules in biological systems. The combined AIM and NBO study permitted us to justify the observed tautomeric preferences. The absolute predominance of the 2H-tautomer forms is greatly changed when the substituent group possesses anionic character; therefore the pH of the medium is relevant. When the calculations were carried out in solution, noteworthy changes in the behavior of charged substituents were observed. These facts may be relevant when studying the interactions of these molecules with biological receptors. (C) 2013 Elsevier B.V. All rights reserved.

引用

页码：31 / 37

页数：7

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