Phenylazoindole dyes - Part I: The syntheses, characterizations, crystal structures, quantum chemical calculations and antimicrobial properties

被引:14
作者
Seferoglu, Zeynel [1 ]
Yalcin, Ergin [1 ]
Babur, Banu [1 ]
Seferoglu, Nurgul [2 ]
Hokelek, Tuncer [3 ]
Yilmaz, Ebru [4 ]
Sahin, Ertan [5 ]
机构
[1] Gazi Univ, Dept Chem, TR-06500 Ankara, Turkey
[2] Gazi Univ, TR-06500 Ankara, Turkey
[3] Hacettepe Univ, Dept Phys, TR-06800 Ankara, Turkey
[4] Gazi Univ, Vocat Sch Hlth Sci, TR-06830 Ankara, Turkey
[5] Ataturk Univ, Dept Chem, Erzurum, Turkey
关键词
Phenylazoindole dye; Azo-hydrazone tautomer; Crystal structure; DFT calculations; Antimicrobial activity; MONOAZO DISPERSE DYE; AZO DYES; DERIVATIVES; ABSORPTION; DECOLORISATION; INDOLE;
D O I
10.1016/j.saa.2013.04.081
中图分类号
O433 [光谱学];
学科分类号
0703 ; 070302 ;
摘要
In this study, the synthesis of four new phenylazo indole dyes (dye 1-4) were carried out by diazotization of 4-aminoacetophenone and coupling with various 2- and 1,2-disubstituted indole derivatives. The dyes were characterized by UV-vis, FT-IR, H-1 NMR, HRMS and X-ray single crystal diffraction methods. Azo-hydrazone tautomeric bahavior of the dyes in different solvents (DMSO, methanol, acetic acid and chloroform) was investigated by using H-1 NMR and UV-vis results. The experimental results were compared with the corresponding calculated values. The results of experimental data and theoretical calculations showed that the azo tautomer is more stable than hydrazone tautomer. In addition to this, the antimicrobial activity of the dyes was also evaluated. Published by Elsevier B.V.
引用
收藏
页码:314 / 324
页数:11
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