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Spectroscopic Studies and Keto-Enol Tautomeric Effect of Newer Schiff Bases of ortho-Hydroxy-benzaldehyde/naphthaldehyde with 1,2-Phenylenediamine and 4-Aminophenyl Ether
Corresponding Author(s) : Ambreen Shah
Asian Journal of Chemistry,
Vol. 25 No. 8 (2013): Vol 25 Issue 8
Abstract
Hydroxyl Schiff bases derived from 1,2-phenylenediamine and 4-aminophenyl ether with o-hydroxy benzaldehyde or o-hydroxyl naphthaldehyde were used to investigate enol-imine and keto-amine tautomeric analysis. UV-visible spectra of the compounds have been investigated tautomeric equilibrium (enol-imine O-H···N, keto- amine O···H-N forms) in different polar and non-polar solvents systems. From FTIR spectra of these model compounds, were possible to assign the IR absorption for the C=O and C=N groups in both keto-amine and enol imine forms, respectively. The keto-enol forms was observed in basic solution of polar and nonpolar solvents such as ethanol, chloroform, DMF, benzene, cyclohexane, n-hexane and in acidic solutions of CHCl3, benzene and n-hexane not in ethanol and DMF. FTIR results were showed that all Schiff bases studied, favoured the enol-imine form over the keto form in a weakly polar solvent.
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References
A.N. Papadopoulos, C.P. Raptopoulou, A. Terzis, A.G. Hatzidimitriou, A. Gourdon and D.P. Kessisoglou, J. Chem. Soc. Dalton Trans, 2591 (1995).
F.S. Kamounah, S.R. Salman and A.A.K. Mahmoud, Spectrosc. Lett., 31, 1557 (1998).
M. Sakamato, Y. Nishida, K. Ohhara, Y. Sadaoka, A. Matsumato and H. Okawa, Polyhedron, 14, 2505 (1995).
S.R. Salman and N.A. Saleh, Spectrosc. Lett., 30, 1289 (1997).
Z. Popovic, V. Roje, G. Pavlovic, D. Matkovic-Calogovic and G. Giester, J. Mol. Struct., 597, 39 (2001).
S.R. Salman, S.H. Shawkat and G.M. Al-Obaidi, Spectrsc. Lett., 31, 221 (1998).
S. Shasad, S.D. Gleb, D.T. Michael and L. Hans-Heinrich, J. Am. Chem. Soc., 128, 3379 (2006).
H. Nazir, M. Yildiz, H. Yilmaz, M.N. Tahir and D. Ulku, J. Mol. Struct., 524, 241 (2000).
T. Hokelek, N. Akduran, M. Yildiz and Z. Kilic, Anal. Sci., 16, 553 (2000).
M. Rospenk, I. Król-Starzomska and A. Filarowski, Chem. Phys., 287, 113 (2003).
H. Unver, M.Yildiz, D.M. Zengin, S. Zbey and E. Kendi, J. Chem. Crystallogr., 31, 211 (2002).
S.H. Alarcón, D. Pagani, J. Bacigalupo and A.C. Olivieri, J. Mol. Struct., 475, 233 (1999).
H. Joshi, F.S. Kamounah, G. van der Zwan, C. Gooijer and L. Antonov, J. Chem. Soc., Perkin Trans. II, 12, 2303 (2001).
R. Harzfeld and P. Nagy, Spectrosc. Lett., 32, 57 (1999).
R. Herzfeld and P. Nagy, Curr. Org. Chem., 5, 373 (2001).
H. Joshi, F.S. Kamounah, C. Gooijer, G. van der Zwan and L. Antonov, J. Photochem. Photobiol. A, 152, 183 (2002).
M. Gavranic, B. Kaitner and E. Mestrovic, J. Chem. Crystallogr., 26, 23 (1996).
H. Ünver, D.M. Zengin and K. Güven, J. Chem. Crystallogr., 30, 359 (2000).
T. Dziembowska, Z. Rozwadowski, A. Filarowski and P.E. Hansen, Magnatic Resonance Chem., 39, 67 (2001).
L. Antonov, M.F. Fabian, D. Nedeltcheva and F.S. Kamounah, J. Chem. Soc., Perkin Trans. II, 1173 (2000).
G.J.M. Fernández, F. del Rio-Portilla, B. Quiroz-García, R.A. Toscano and R. Salcedo, J. Mol. Struct., 561, 197 (2001).
S.D. Chatziefthimiou, Y.G. Lazarou, E. Hagjoudis, T. Dziembowska and I.M. Mavridis, J. Phys. Chem. B, 110, 23701 (2006).
J. Zawadiak and M. Mrzyczek, Spectrochim. Acta A, 75, 925 (2010).
D. Yanagissawa and N. Shirai, Biomaterial, 31, 4179 (2010).
S. Samal, R.R. Das, D. Sahoo, S.Acharya, R.L. Panda and R.C. Rout, J. Appl. Polym. Sci., 62, 1437 (1996).