Tautomeric structures of some 2-arylazo-1-hydroxycyclohex-1-en- 3-one: Spectroscopic investigations and theoretical studies

Canadian Journal of Analytical Sciences and Spectroscopy

Volumn 53, Issue 6, 2008, Pages 282-293

  Ebead, Y H ^a   Fandy, R F ^a   Zayed, S E ^a   Abd Elshafi, E ^a   Ibrahim, S A ^b  

^a SOUTH VALLEY UNIVERSITY   (Egypt)

^b Assiut University   (Egypt)

Author keywords

Azo dyes; NMR and electronic absorption spectra; Tautomerism; Theoretical calculations

Indexed keywords

EID: 72349085257     PISSN: 12056685     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (71)

1. K.Venkataraman, "The Chemistry of Synthetic Dyes Vol. I", Academic Press, New York, 1952, p. 551.
2. S. Patia, "The Chemistry of the Hydrazo and Azoxy Groups", John Wiley&Sons, London, 1975.
3. F. Chiraleu, V. Cimpeanu, Dyes Pigments, 57, 223 (2003).
4. N.M. Rageh, Spectrochim. Acta A, 60, 1917 (2004).
5. A.K. Flatt, S.M. Dirk, J.C. Henderson, D.E. Shen, J. Su, M.A. Reed, J.M. Tour, Tetrahedron, 59, 8555 (2003).
6. J.S. Tao, J.F. Biernat, V.C. Kravtsov, Y.A. Simonov, Tetrahedron, 55, 8433 (1999).
7. A.R.H.M. Yousoff, A.G. Fogg, R. Ahmed, Talanta 47, 797 (1998).
8. S.A. Langford, J.K. Sugden, R.W. Fitzpatrick, J. Pharm. Biomed. Anal., 14, 1615 (1996).
9. P. Rajaguru, L. Vidya, B. Baskarasethupathi, P.A. Kumar, M. Palanivel, K. Kalaiselvi, Mutat. Res., 517, 29 (2002).
10. A. Eriksson, L. Nyholm, Electrochim. Acta, 44, 4029 (1999).
11. Y. Cheng, M. Zhang, H. Yang, F. Li, T. Yi, C. Huang, Dyes Pigments, 76, 775 (2008).
12. K.L. Georgiadou, E.G. Tsatsaroni, Dyes Pigments, 50, 93 (2001).
13. T. Konstantinova, P. Petrova, Dyes Pigments, 52, 115 (2002).
14. M. Humphreys, N. Hall, D.A.S. Phillips, J.A. Taylor, Dyes Pigments, 59, 193 (2003).
15. J.J. Lee, W.J. Lee, J.H. Choi, J.P. Kim, Dyes Pigments, 65, 75 (2005) and references therein.
16. A.B. dos Santos, F.J. Cervantes, J.B. van Lier, Bioresource Technol., 98, 2369 (2007).
17. S. Shibata, in: H. Flaschka, A.J. Bornared, "Chelates in Analytical Chemistry Vol. 4", Marcel Dekker, New York, 1972.
18. A. Amin, Anal. Lett., 32, 1575 (1999).
19. R.D. Voyksner, Anal. Chem., 57, 2600 (1985).
20. M. Perez, M.D. Part, J.L. Beltran, J. Chromatogr. A, 871, 227 (2000).
21. A. Natansohn (Ed), "Azobenzene-Containing Materials", Wiley-VCH Weinheim, 1999.
22. A. Pourjavadi, B.F. Mirjalili, A.A. Entezam, M.J. Zohuriaan-Meher, Eur. Poly. J., 37, 2111 (2001).
23. Y. Chen, Q. Gong, F. Wang, B. Zang, Z. Chen, Mater. Lett., 57, 4372 (2003).
24. M. Jin, Q.X. Yang, R. Lu, L.Y. Pan, P.C. Xue, Y.Y. Zhao, Opt. Mater., 24, 445 (2003).
25. M. Saminathan, C.K.S. Pillai, Polymer, 41, 3103 (2000).
26. G. Zotti, S. Zecchin, G. Schivaon, A. Berlin, G. Pagani, A. Canavesi, G.C. Miceli, Synth. Met., 78, 51 (1996).
27. N.S. Al-Muaikel, T.I. El-Emary, Eur. Poly. J., 39, 211 (2003).
28. S. Wang, S. Shen, H. Xu, Dyes Pigments, 44, 195 (2000).
29. A.K. Sikder, N. Sikder, J. Hazard. Mater. A, 112, 1 (2004).
30. D.E. Fenton, "Advanced in Inorganic and Bioorganic Mechanisms Vol. 2", Ed. A.J. Sykes, Academic Press, London, 1983.
31. G.A. Ibannez, G.M. Escandar, Polyhedron, 17, 4433 (1998).
32. F.C. de Abreu, F.S. de Paula, A.F. dos Santos, A.E.G. Sant'Ana, M.V. de Almeida, E.T. Cesar, M.N. Trindade, M.O.F. Goulart, Bioorg. Med. Chem., 9, 659 (2001).
33. S.H. Alarcon, A.C. Olivieri, D. Sanz, R.M. Claramunt, J. Elguero, J. Mol. Struct., 705, 1 (2004).
34. F. Langa, P. de la Cruz, J.L. Delgado, M.M. Haley, L. Shirtchliff, I. Alkorta, J. Elguero, J. Mol. Struct. 699, 17 (2004).
35. N.M. Rageh, A.A. Mohamed, H.M.S. Elkashef, S.A. Ibrahim, Y.H. Ebead, Can. J. Spectrosc., 43, 6 (1999).
36. S. Tauro, E.Coutinho, J. Mol. Struct. (Theochem), 532, 23 (2000).
37. M. Sahu, M.B. Saha, S.C. Bera, J. Photochem. Photobiol. A: Chem., 89, 19 (1995).
38. B. Feringa, W. Jager, B. Lange, Tetrahedron Lett., 49, 8276 (1993).
39. J.K. Labanowski, J.W. Andzelm (Eds), "Density Functional Methods in Chemistry", New York, Spring Verlag, 1991.
40. J. Baker, J. Comput. Chem., 7, 385 (1986).
41. H.B. Schlegel (Ed), "Modern Electronic Structure Theory: Geometry Optimization on Potential Energy Surfaces", Singapore, World Scientific, 1994.
42. M.M. Francl, W.J. Pietro, W.J. Hehre, J.S. Binkle, M.S Gordon, D.J. Defrees, J.A. Pople, J. Chem. Phys., 77, 3645 (1972).
43. P.C. Hariharan, J.A. Pople, Theor. Chim. Acta, 28, 213 (1973).
44. A.D. Becke, Phys. Rev. A, 38, 3098 (1988).
45. A.D. Becke, J. Chem. Phys., 98, 1372 (1993).
46. C. Lee, W. Yang, R.G. Parr, Phys. Rev. B, 37, 785 (1988).
47. N.C. Handy, D.J. Tozer, G.J. Laming, C.W. Murray, R.D. Amos, Isr. J. Chem., 33, 331 (1993).
48. R. Ditchfield, Mol. Phys., 27, 789 (1974).
49. K.Wolinski, J.A. Hinton, P. Pulay, J. Am. Chem. Soc., 112, 8251 (1990).
50. J. Gauss, J. Chem. Phys., 99, 3629 (1993).
51. K.M. Tait, J.A. Parkinson, A.C. Jones, W.J. Ebenezer, S.P. Bates, Chem. Phys. Lett., 347, 372 (2003).
52. E. Kleinpeter, A. Koch, G. Fischer, C.P. Askolin, J. Mol. Struct., 435, 65 (1997).
53. D. Maciejewska, I. Wolska, V. Kowalska, J. Mol. Struct., 693, 27 (2004).
54. A. Kaczor, L.M. Proniewicz, J. Mol. Struct. (Theochem), 640, 133 (2003).
55. Y. Ebead, A. Wroblewska, K. Krzyminski, J. Rak, J. Blazejowski, J. Phys. Org. Chem., 18, 870 (2005).
56. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision D.01, Gaussian, Inc., Wallingford CT, 2004.
57. B. Vickery, G.R. Willey, M.G.B. Drew, J. Chem. Soc., Perkin Trans. 2, 1454 (1981).
58. M.G.B. Drew, B. Vickery, G.R. Willey, J. Chem. Soc., Perkin Trans. 2, 1297 (1982).
59. B. Vickery, G.R. Willey, M.G.B. Drew, J. Chem. Soc., Perkin Trans. 2, 155 (1981).
60. V.T. Rema, K. Krishnankutty, J. Michael, J. Indian Chem. Soc., 74, 391 (1997).
61. M. Dakiky, I. Memcova, Dyes Pigments, 40, 141 (1999).
62. H. Kocaokutgen, S. Özkinali, Dyes Pigments, 63, 83 (2004).
63. M.R. Yazdanbakhsh, A.Ghanadzadeh, E. Moradi, J. Mol. Liq., 136, 165 (2007).
64. X.L.You, C. Lu, Z.L. Huang, D.C. Zhang, Dyes Pigments, 63, 217 (2004).
65. G.N. Ledesma, G.A. Ibanez, G.M. Escandar, A.C. Olivier, J. Mol. Struct., 415, 115 (1997).
66. J. Elguero, R. Jacquier, G. Tarrago, Bull. Soc. Chim. France, 281 (1966).
67. F. Kaberia, B. Vickery, G.R. Willey, M.G.B. Drew, J. Chem. Soc., Perkin Trans. 2, 1622 (1980) and references 4-9 therein.
68. P. Simunek, V. Bertolasi, V. Machacek, J. Mol. Struct., 642, 41 (2002).
69. A. Lycka, Dyes Pigments, 43, 27 (1999).
70. G. Briegleb "Electron Donor-Acceptor Komplex" Springer Verlag, Berlin, 1961.
71. M.M.A. Hamed, N.M. Ismail and S.A. Ibrahim, Dyes Pigments, 26, 297 (1994).