Quantum-chemical calculations, tautomeric, thermodynamic, spectroscopic and X-ray studies of 3-(4-fluorophenylhydrazone)pentane-2,4-dione

被引：53

作者：

Maharramov, Abel M. ^{[1
]}

Aliyeva, Rafiga A. ^{[1
]}

Aliyev, Ismayil A. ^{[1
]}

Pashaev, Faig H. ^{[1
]}

Gasanov, Arzuman G. ^{[1
]}

Azimova, Saida I. ^{[1
]}

Askerov, Rizvan K. ^{[1
]}

Gurbanov, Atash V. ^{[1
]}

Mahmudov, Kamran T. ^{[1
]}

机构：

[1] Baku State Univ, Dept Chem, Zkhalilov 23, Azerbaijan

来源：

DYES AND PIGMENTS | 2010年 / 85卷 / 1-2期

关键词：

3-(4-Fluorophenylhydrazone)pentane-2,4-dione; Hydrogen bonding; Hydrazone dyes; Tautomeric studies; X-ray characterization; Thermodynamic parameters; Quantum-chemical calculations; STABILITY-CONSTANTS; METAL COMPLEXATION; PROTON-TRANSFER; RESONANCE; INTERCORRELATION; BENZOYLACETONE; ACETYLACETONE; COPPER(II); PARAMETERS; FORMS;

D O I：

10.1016/j.dyepig.2009.09.003

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The structural and tautomeric characteristics of 3-(4-fluorophenylhydrazone)pentane-2,4-dione were studied using 1R. H-1 and C-13 NMR spectroscopy. X-ray diffraction analysis and quantum-chemical calculations. Crystallographic data shows that the compound has a hydrazone structure that contains intramolecular H-bonds assisted by resonance, with a N-O distance of 2.5872 angstrom. The effective atomic charges in the tautomeric forms of the colorant (enol-azo, keto-azo and hydrazone), Was Calculated using an MO LCAO quantum-chemical method employing the Huckel approximation, the compound was stabilized in the hydrazone form and displayed high reactivity The thermodynamic functions of the proton dissociation constant of the colorant were determined by potentiometry: the dissociation process was unspontaneous, endothermic and entropically unfavorable. The findings reveal that the colorant has the same structure in both DMSO solution and the solid state. (C) 2009 Elsevier Ltd. All rights reserved

引用

页码：1 / 6

页数：6

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