The syntheses, structures and azo–hydrazone tautomeric studies of three triazole/tetrazole azo dyes. (3rd October 2016)

• Record Type: Journal Article
• Authors: Cai, Jiawei; Li, Zhixin; Qiu, Yanxuan; OuYang, Zhijian; Lin, Wenning; Yang, Liu; Feng, Weijin; Yu, Xinwei; Dong, Wen
• Is Part Of: New journal of chemistry. Volume 40:Number 11(2016:Nov.)
• Page Start: 9370
• Page End: 9379
• Publication Date: 2016-10-03
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c5nj02539g
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : The azo–hydrazone tautomerism for three triazole/tetrazole azo dyes can be elucidated by 1 H, 13 C NMR and UV-vis spectra. Abstract : Three heterocyclic azo dyes of azotriazolyl-2, 7-dihydroxynaphthalene (H3 AD), azotetrazolyl-2-naphthol (H2 ATN) and azotetrazolyl-2, 7-dihydroxynaphthalene (H3 ATD) have been synthesized and characterized by IR, Raman spectra, 1 H, 13 C NMR and X-ray single-crystal diffraction techniques and their azo–hydrazone tautomerism has been achieved by pH control and coordination-coupled proton transfer. UV-vis spectra have been used to monitor the pH-titration and metal-ion complex experiments for three solutions of H3 AD, H2 ATN and H3 ATD and the analysis of their spectral data has provided a clear proof that the hydrazone form is the dominant tautomer in acidic and neutral solutions, while the azo form is the dominant one in alkaline solutions. Crystallographic data demonstrate that the neutral dyes exist as hydrazone tautomers but are changed to azo tautomers when they coordinate to metal ions. The time-dependent density functional theory (TD-DFT) calculations are used to demonstrate the UV-vis spectroscopic properties.