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AASCIT Communications | Volume 2, Issue 6 | Oct. 28, 2015 online | Page:286-292
Solvatochromism of Indolino Spirobenzoxazine and Its Azo-Substituted Derivative: Comparison of Solvent Polarity Scales of Kamlet-Taft and Catalan
The solvatochromic behavior of the electronic absorption spectra of indolino spirobenzoxazine and its azo derivative were investigated in polar and non-polar solvents. A bathochromic shift of about 10 nm in the electronic spectra of both compounds was observe as the solvent polarity increases from benzene to ethanol. The presence of an azo group substituted at the oxazine fragment of indolino spirobenzoxazine exhibited a bathochromic shift of about 50 nm in all the solvents studied. The results obtained from single parametric regression analysis using both Kamlet-Taft and Catalan solvent parameters indicate that Kamlet-Taft scale is most suitable in describing hydrogen bond donor acidity and hydrogen bond acceptor basicity interactions whereas Catalan scale is a better descriptor of dipolarity and polarizability interactions. This shows that no one solvent polarity scale is adequate to describe all the solute-solvent interactions of molecular electronic absorption.
Victor N. Mkpenie, Department of Chemistry, University of Uyo, Uyo, Nigeria.
Emmanuel E. Essien, Department of Chemistry, University of Uyo, Uyo, Nigeria.
Solvatochromism, Kamlet-Taft, Catalan, Polarity scales, Azo, Spirobenzoxazine
Rao, C.N.R., Singh, S., Senthilnathan, V.P. Spectroscopic studies of solute-solvent interactions. Chem. Soc. Rev., 1976, 5: 297-316.
Bakhshiev, N.G. Universal intermolecular interactions and their effect on the position of the electronic spectra of molecules in two component solutions. Opt. Spectrosk., 1962, 13: 24-29.
Baur, M.E., Nicol M. Solvent stark effect and spectral shifts. J. Chem. Phys., 1966, 44: 3337-3344.
Kamlet, M.J., Abboud, J.L.M., Abraham, M.H., Taft, R.W. Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, π*, α and β, and some methods for simplifying the generalized solvatochromic equation. J. Org. Chem., 1983, 48: 2877–2887.
J. Catalan, and C. Diaz, “Extending the solvent acidiy scale to highly acidic organic solvents: The unique photophysical behaviour of 3,6-diethyltetrazine”, Eur. J. Org. Chem., 1999, pp. 885–891.
Papadakis, R., Deligkiozi, I., Tsolomitis, A. Spectroscopic investigation of the solvatochromic behavior of a new synthesized non symmetric viologen dye: study of the solvent-solute interactions. Anal Bioanal Chem., 2010, 397(6): 2253-2259.
Baruah, M., Qin, W., Flors, C., Hofkens, J., Vall´ee, R.A.L., Beljonne, D., Auweraer, M.V.D., Borggraeve, W.M.D., Boens, N. Solvent and pH dependent fluorescent properties of a dimethylaminostyryl borondipyrromethene dye in solution. J. Phys. Chem. A, 2006, 110: 5998–6009.
Homocianu, M., Airinei, A., Dorohoi, D.O., Olariu, I., Fifere, N. Solvatochromic effects in the UV/vis absorption spectra of some pyridazinium ylides. Spectrochim. Acta. A Mol. Biomol. Spectrosc., 2011, 82(1): 355-359.
Rauf, M.A., Soliman, A.A., Khattab ,M. Solvent effect on the spectral properties of Neutral Red. Chem Cent J. 2008, 2: 19-26. doi: 10.1186/1752-153X-2-19.
Sancho, M.I., Almandoz, M.C., Blanco, S.E., Castro, E.A. Spectroscopic study of solvent effects on the electronic absorption spectra of flavone and 7-hydroxyflavone in neat and binary solvent mixtures. Int. J. Mol. Sci., 2011, 12(12): 8895–8912.
Oliveira, C.S., Branco, K.P., Baptista, M.S., Indig, G.L. Solvent and concentration effects on the visible spectra of tri-para-dialkylamino-substituted triarylmethane dyes in liquid solutions. Spectrochim. Acta. A Mol. Biomol. Spectrosc., 2002, 58(13): 2971-2982.
Harifi-Mood, A.R., Habibi-Yangjeh, A., Gholami, M.R. Solvatochromic parameters for binary mixtures of 1-(1-butyl)-3-methylimidazolium tetrafluoroborate with some protic molecular solvents. J. Phys. Chem. B. 2006, 110(13): 7073-7078.
Azizi, S.N., Chaichi, M.J., Yousefi, M. Investigation of solvent effects on UV-vis absorption spectra of dihydroxybenzene derivatives by solvatochromic parameters. Spectrochim. Acta. A Mol. Biomol. Spectrosc., 2009, 73(1): 101-105.
Mkpenie, V.N., Mkpenie, I.V. The Effects of solvent and pH on the electronic spectral properties of indolino spirobenzoxazine. International Research Journal of Pure & Applied Chemistry, 2016, 10(1): 1-7. doi: 10.9734/IRJPAC/2016/19768.
Masoud, M.S., Hagagg, S.S., Ali, A.E., Nasr, N.M. Solvatochromic behavior of the electronic absorption spectra of gallic acid and some of its azo derivatives. Spectrochim. Acta. A Mol. Biomol. Spectrosc., 2012, 94: 256-264.
Gülseven, S.Y., Sıdır, I., Taşal, E., Ermiş, E. Studies on the electronic absorption spectra of some monoazo derivatives. Spectrochim. Acta. A Mol. Biomol. Spectrosc., 2011, 78(2): 640-647.
Mkpenie, V.N., Essien, E.E., Ita, B.N. Synthesis and biological activities of indolino spirobenzoxazine. J. Chem. Pharm. Res. 2015, 7(5): 787-789.
Mkpenie, V., Ebong, G., Obot, I.B., Abasiekong, B. Evaluation of the effect of azo group on the biological activity of 1-(4-methylphenylazo)-2-naphthol. E-J Chem., 2008, 5(3): 431-434.
Sherif, O.E. Effect of solvents on the electronic absorption spectra of some substituted diarylformazans. Monatchefter für Chemie., 1997, 128: 981-990.
Whitten, K.W., Gailey, K.O. General chemistry with quality analysis. Philadelphia: Saunders College Publishing; 1981.
Chu, N.Y.C. 4N+2 Systems, spirooxazines. In: Durr, H., Laurent, H.B., (editors). Photochromism, molecules and systems. Amsterdam: Elseiver; 1990.
Marcus, Y. The properties of solvents. In: Fogg, P.G.T. (editor). Wiley series in solution chemistry. Vol. 4. New York: John Wiley and Sons Ltd; 1998.
Reichardt, C. Solvatochromic dyes as solvent polarity indicators. Chem Rev. 1994, 94(8): 2319-2358.
Dimroth, K., Reichardt, C. Pyridinium-N-phenol betaines and their application for the characterization of solvent polarities. Extension of the solvent polarity scale by application of alkyl-substituted pyridinium- N-phenol betaines. Liebigs. Ann. Chem., 1969, 727(1): 93-105.
Fowler, F.W., Katritzky, A.R., Rutherford, R.J.D. The correlation of solvent effects on physical and chemical properties. J. Chem. Soc. Part B. 1971: 460-469.
Reichardt, C., Harbusch-Gornert, E. Pyridinium-N-phenoxide betaines and their application for the characterization of solvent polarities, X. – Extension, correction, and new definition of the ET solvent polarity scale by application of a lipophilic penta-tert -butyl-substituted pyridinium-N-phenoxide betaine dye. Liebigs. Ann. Chem., 1983, (5): 721-743.
Bahera, P.K., Xess, A., Sahu, S. Solvent effects on the electronic spectra of some heterocyclic azo dyes. Bull. Korean Chem. Soc., 2014, 35(2): 610-616.
Kosower, E.M., Skorcz, J.A., Schwarz, W.M., Patton, J.W. Pyridinium complexes. I. The significance of the second charge-transfer band of pyridinium iodides. J. Am. Chem. Soc. 1960, 82: 2188-2191.
Arcticle History
Submitted: Oct. 14, 2015
Accepted: Oct. 20, 2015
Published: Oct. 28, 2015
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