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A novel azocompound, 2-(4-phenylazoaniline)-4-phenylphenol: Spectroscopic and quantum-chemical approach
Article first published online: 30 MAY 2012
Copyright © 2012 Wiley Periodicals, Inc.
International Journal of Quantum Chemistry
Volume 113, Issue 8, pages 1107–1115, 15 April 2013
How to Cite
Nicolás-Vázquez, I., Pérez-Caballero, G., Jiménez, A. G., Rangel, G. G. and Ruvalcaba, R. M. (2013), A novel azocompound, 2-(4-phenylazoaniline)-4-phenylphenol: Spectroscopic and quantum-chemical approach. Int. J. Quantum Chem., 113: 1107–1115. doi: 10.1002/qua.24171
- Issue published online: 6 MAR 2013
- Article first published online: 30 MAY 2012
- Manuscript Accepted: 17 APR 2012
- Manuscript Revised: 13 APR 2012
- Manuscript Received: 26 JAN 2012
- DFT and AIM calculations;
A novel azocompound with two nonequivalents azo groups, 2-(4-phenylazoaniline)-4-phenylphenol, was synthesized and characterized by spectroscopic and computational analysis. An intramolecular hydrogen bonding (HB), O1H1···N1, involving the N1N2 group and the proton in a neighbor hydroxyl moiety, was identified. It was found responsible for a characteristic π-conjugated H1O1C18C13N2N1 six-membered cyclic fragment. It is worth noting that this azo group is involved in an azo-hydrazo equilibrium, being the azo form the most stable one. This resonance-assisted HB was characterized using the OH-related infrared bands and the corresponding signals in 1H NMR. In addition, conformational studies and geometrical and electronic parameter calculations were performed using the density functional theory, at B3LYP/6-311++G** level. Bond and ring critical points were identified using the atoms in molecules theory, which allowed confirming the intramolecular HB. The second azo-group cannot be involved in HB, but it also presents two stereoisomerics forms corresponding to cis (Z) and trans (E) configurations, with the later being the one with the lowest energy. © 2013 Wiley Periodicals, Inc.