The synthesis, characterization and structures of some 4-[((E)-1-{2-hydroxy-5-[(E)-2-(aryl)-1-diazenyl]phenyl}methylidene)amino]benzoic acid

被引：24

作者：

Baul, Tushar S. Basu ^{[1
]}

Das, Pradip ^{[1
]}

Chandra, Asit K. ^{[1
]}

Mitra, Sivprasad ^{[1
]}

Pyke, Simon M. ^{[2
]}

机构：

[1] NE Hill Univ, Dept Chem, Shillong 793022, Meghalaya, India

[2] Univ Adelaide, Fac Sci, Sch Chem & Phys, Adelaide, SA 5005, Australia

来源：

DYES AND PIGMENTS | 2009年 / 82卷 / 03期

关键词：

Azo-dyes; 4-[((E)-1-{2-Hydroxy-5-[(E)-2-(aryl)-1-diazenyl]phenyl}methylidene)amino]benzoic acid; NMR; UV-VIS spectroscopy; DFT calculation; Structures; SCHIFF-BASES; TRIPHENYLTIN(IV) COMPLEXES; TRIBUTYLTIN(IV) COMPLEXES; MAGNETIC-PROPERTIES; THERMAL-PROPERTIES; CRYSTAL-STRUCTURES; CU(II) COMPLEXES; MOSQUITO LARVAE; PROTON-TRANSFER; AZO;

D O I：

10.1016/j.dyepig.2009.02.012

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The structures of several azo-benzoic acids, 4-[((E)-1-{2-hydroxy-5-[(E)-2- (aryl)-1-diazenyl]phenyl}methylidene)amino]benzoic acid along with their precursors 2-hydroxy-5-[(E)-(aryldiazenyl)]benzaldehydes were confirmed using (1)H, (13)C NMR, UV-VIS and IR spectroscopic techniques. UV-VIS absorption spectra were measured in pure organic solvents while complementary spectroscopic experiments using mixed solvent systems as well as in the presence of base were undertaken to characterize the different species present in solution. Both acid-base dissociation and azo-hydrazone tautomerism occurred in solution, with the extent of the individual equilibria being dependent on the solvent composition and/or pH of the medium. Molecular structures and geometries were optimized using the B3LYP density functional theory method employing the 6-31G(d) basis set. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：379 / 386

页数：8

共 34 条

[11] SPECTRAL, THERMAL AND MAGNETIC-PROPERTIES OF NI(II) COMPLEXES OF PARA-PHENYLAZO-SALICYLALDEHYDES [J].

DESHMUKH, KG ;

BHOBE, RA .

JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1978, 40 (01) :135-136

[12]

DESHMUKH KG, 1977, CURR SCI INDIA, V46, P67

[13]

DESHMUKH KG, 1977, J INDIAN CHEM SOC, V54, P375

[14]

GONCHARUK VV, 1981, THEORETICAL EXPT CHE, V16, P330

[15] PROTON-TRANSFER ALONG THE INTERNAL HYDROGEN-BONDS IN EXCITED SCHIFF-BASES - PHOTOCHROMISM IN SYMMETRICAL SYSTEMS WITH 2 EQUIVALENT REACTION SITES [J].

GRABOWSKA, A ;

KOWNACKI, K ;

KACZMAREK, L .

JOURNAL OF LUMINESCENCE, 1994, 60-1 :886-890

[16] Excited state intramolecular proton transfer in some tautomeric azo dyes and Schiff bases containing an intramolecular hydrogen bond [J].

Joshi, H ;

Kamounah, FS ;

Gooijer, C ;

van der Zwan, G ;

Antonov, L .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2002, 152 (1-3) :183-191

[17] Preparation and thermal properties of the bis[5-((4-heptyl oxyphenyl)azo)-N-(4-alkoxyphenyl)-salicylaldiminato]copper(II) complex homologues [J].

Khandar, AA ;

Rezvani, Z .

POLYHEDRON, 1998, 18 (1-2) :129-133

[18] Synthesis and characterization of a series of copper(II) complexes with azo-linked salicylaldimine Schiff base ligands.: Crystal structure of Cu5PHAZOSALTN•CHCl3 [J].

Khandar, AA ;

Nejati, K .

POLYHEDRON, 2000, 19 (06) :607-613

[19] Role of structural flexibility in the fluorescence and photochromism of salicylideneaniline: the general scheme of the phototransformations [J].

Kletskii, ME ;

Millov, AA ;

Metelitsa, AV ;

Knyazhansky, MI .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1997, 110 (03) :267-270

[20] DEVELOPMENT OF THE COLLE-SALVETTI CORRELATION-ENERGY FORMULA INTO A FUNCTIONAL OF THE ELECTRON-DENSITY [J].

LEE, CT ;

YANG, WT ;

PARR, RG .

PHYSICAL REVIEW B, 1988, 37 (02) :785-789

← 1 2 3 4 →