Ab initio modeling of the solvent influence on the azo-hydrazone tautomerism

被引：54
作者：
Antonov, L
Kawauchi, S
Satoh, M
Komiyama, J
机构：
[1] Natl Foresty Univ, Dept Ecol, Sofia 1756, Bulgaria
[2] Tokyo Inst Technol, Dept Polymer Sci, Meguro Ku, Tokyo 152, Japan
来源：
DYES AND PIGMENTS | 1999年 / 40卷 / 2-3期
关键词：
tautomerism; azo dyes; hydrogen bonding; solvent effect;
D O I：
10.1016/S0143-7208(98)00044-8
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The solvent effect on the azo (A) -hydrazone (H) tautomeric equilibrium of 1-phenylazo-4-naphthol is modeled by using ab initio quantum-chemical calculations. It was found that in methanol, methylene chloride and water there exists a strong hydrogen bonding between the particular tautomer and solvent, as well as dipole-dipole dye-solvent interactions. The results show that the H-form is more stable in water and methylene chloride, while methanol and i-octane stabilize the A-form. The calculational results obtained are in very good agreement with the experimental data in these solvents published previously. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码：163 / 170
页数：8
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