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

[1] New scale factors for harmonic vibrational frequencies using the B3LYP density functional method with the triple-ξ basis set 6-311+G(d,p)
Andersson, MP
Uvdal, P
[J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2005, 109 (12) : 2937 - 2941
[2] TAUTOMERIC EQUILIBRIUM IN 1-PHENYLAZO-2-NAPHTHOL - A QUANTITATIVE STUDY
ANTONOV, L
STOYANOV, S
STOYANOVA, T
[J]. DYES AND PIGMENTS, 1995, 27 (02) : 133 - 142
[3] AZO-HYDRAZONE TAUTOMERISM OF HYDROXYAZO COMPOUNDS - A REVIEW
BALL, P
NICHOLLS, CH
[J]. DYES AND PIGMENTS, 1982, 3 (01) : 5 - 26
[4] Embryotoxicity studies of tri-n-butyltin(IV) complexes of 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoic acid and 2-[(E)-2-(3-formyl-4-hydroxyphenyl)-1-diazenyl] benzoic acid on sea urchin development
Baul, TSB
Rynjah, W
Singh, KS
Pellerito, C
D'Agati, P
Pellerito, L
[J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2005, 19 (11) : 1189 - 1195
[5] Electrospray ionization mass spectrometry of tributyltin(IV) complexes and their larvicidal activity on mosquito larvae:: crystal and molecular structure of polymeric (Bu3Sn[O2CC6H4{N=N(C6H3-4-OH (C(H)= NC6H4OCH3-4))}-o])n
Baul, TSB
Singh, KS
Holcapek, M
Jirásko, R
Linden, A
Song, XQ
Zapata, A
Eng, G
[J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2005, 19 (08) : 935 - 944
[6] Synthesis and characterization of tributyltin(IV) complexes of 2-[(E)-2-(3-formyl-4-hydroxyphenyl)-1-diazenyl]benzoic acid and 4-[((E)-1-{2-hydroxy-5-[(E)-2-(2-carboxyphenyl)-1-diazenyl]phenyl}methylidene)amino]aryls -: crystal structures of polymeric (Bu3Sn[O2CC6H4{N=N(C6H3-4-OH-5-CHO)}-o])n and (Bu3Sn[O2CC6H4{N=N(C6H3-4-OH-C(H)=NC6H4Cl-4))}-o])n -: toxicity studies on the second instar of Aedes aegypti mosquito larvae
Baul, TSB
Singh, KS
Song, XQ
Zapata, A
Eng, G
Lycka, A
Linden, A
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (25) : 4702 - 4711
[7] Synthesis, characterization and crystal structures of polymeric. and dimeric triphenyltin(IV) complexes of 4-[((E)-1-{2-hydroxy-5-[(E)-2-(2-carboxyphenyl)-1-diazenyl]phenyl}methylidene)amino]aryls
Baul, TSB
Singh, KS
Holcapek, M
Jirásko, R
Rivarola, E
Linden, A
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (19) : 4232 - 4242
[8] A quasi-planar polyaromatic compound containing an azo and a Schiff base linkage
Butcher, RJ
Baul, TSB
Singh, KS
Smith, FE
[J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O1007 - O1009
[9] STABILITY OF CHELATE COMPOUNDS
CALVIN, M
WILSON, KW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1945, 67 (11) : 2003 - 2007
[10] DASMOHAN PN, 1972, J INDIAN CHEM SOC, V49, P739

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