Study of the Azo Hydrazone Tautomerism in the 4-(9-Anthrylazo) Phenol

Authors: Ramadan Ali Bawa, Ebtisam Mohammed Alzaraide

Abstract:

The spectroscopic study on 4-(9-anthrylazo) phenol has revealed that the azo dye under study exists in two tautomeric forms which are azo phenol and hydrazo keto forms in ratio of almost (1:1). The azo hydrazone tautomerism was confirmed by the use of IR spectroscopy and HNMR in which the characteristic absorption bands and chemical shifts for both tautomers were assigned.

Keywords: Spectroscopic, tautomeric forms, azo hydrazone tautomerism, IR spectroscopy, HNMR.

Digital Object Identifier (DOI): doi.org/10.5281/zenodo.1091980

References:

[1] F. Van der Zee ; Anaerobic Azo Dye Reduction, 2002, Thesis Wagningen Universety, Wagningen, Netherlands, pp 2 – 7, 32, 33, 84.
[2] H. Erkurt; Biodegradation of Azo Dyes, Spring-Verlag, Berlin Heidelberg, Germany, 2010, Vol. 9, pp 40 – 42.
[3] M. Aziz and H. El-Mallah, "Electrical and optical properties of azo dye”, Indian Journal of Pure and Applied Physics, vol. 47, 2009, pp 530 - 534.
[4] S. Yin, H. Xu, W. Shi, Y. Gao, Y. Song, J. Lam and B. Tang, "Synthesis and optical properties of polyacetylenes containing nonlinear optical chromophores”, Polymer, vol. 46, 2005, pp. 7670 – 7677.
[5] A. Pielesz, "The process of the reduction of azo dyes used in dyeing textiles on the basis of infrared spectroscopy analysis”, J. Mol. Struct., vol. 511-512, 1999, pp. 337 – 344.
[6] N.A. Oranusi, C.J. Ogugbue, "Effect of pH and Nutrient Starvation on Biodegradation of Azo Dyes by Pseudomonas”, J. Appl. Sci. Environ. Mgt., vol. 9, 2005, pp. 39 – 43.
[7] G. Hallas, J.-H. Choi, "Synthesis and properties of novel aziridinyl azo dyes from 2-aminothiophenes—Part 2: Application of some disperse dyes to polyester fibers” Dyes Pigm., vol. 40, 1999, pp. 119 – 129.
[8] M.A. Weaver, L. Shuttleworth, "Heterocyclic diazo components”, Dyes Pigm., vol. 3, 1982, pp. 81 – 121.
[9] Y. Cheng, M. Zhang, H. Yang, F. Li, T. Yi, C. Huang,. "Azo dyes based on 8-hydroxyquinoline benzoates: Synthesis and application as colorimetric Hg2+-selective chemosensors”, Dyes Pigm., vol. 76, 2008, pp. 775 – 783.
[10] P. Kaur, S. Kaur, A. Mahajan, K. Singh,. "Highly selective colorimetric sensor for Zn2+ based on hetarylazo derivative”, Inorg. Chem. Commun., vol. 11, 2008, pp. 626 – 629.
[11] M.M.M. Raposo, M.C.R. Castro, M. Belsley, A.M.C. Fonseca, "Push–pull bithiophene azo-chromophores bearing thiazole and benzothiazole acceptor moieties: Synthesis and evaluation of their redox and nonlinear optical properties”, Dyes Pigm., 2011, 91, 454 – 465.
[12] A. S. Ozen, P. Doruker and V. Aviyente, "Effect of Cooperative Hydrogen Bonding in Azo-Hydrazone Tautomerism of Azo Dyes”, J. Phys. Chem. A., vol. 111, 2007, pp. 13506 – 13514.
[13] R. A. Bawa, E. M. Alzaraide and N. N. Ben Ehmidah, "Synthesis and electric conductivity study of the new azo dye 4-(9-anthrylazo)phenol”, Int. Journal of Engineering Research and Application, vol. 3, 2013, pp. 1 – 5.
[14] I. Mohammed and A. Mustapha; "Synthesis of new azo compounds based on N-(4-hydroxypheneyl)maleimide and N-(4-methylpheneyl)maleimide”, Molecules, vol. 15, 2010, pp. 7498 – 7508.
[15] R. A. Bawa, E. J. Zaghloot, K. E. Mossa and N. O. Issa; "Synthesis and electric conductivity study of 4-(p-aminophenylazo) benzene sulphonic acid”, Journal of Materials Science and Engineering B, vol. 3, 2013, pp. 167 – 170.