How to drive imine-enamine tautomerism of pyronic derivatives of biological interest - A theoretical and experimental study of substituent and solvent effects

Comptes Rendus Chimie

Volumn 13, Issue 5, 2010, Pages 553-560

  Amar, Anissa ^a   Meghezzi, Hacene ^a   Boucekkine, Abdou ^b   Kaoua, Racheddine ^a   Kolli, Bellara ^a  

^a UNIVERSITY OF SCIENCES AND TECHNOLOGY HOUARI BOUMEDIENE   (Algeria)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

DFT; Imine enamine; NBO; Solvent effect; Substituted pyrones; Tautomerism

Indexed keywords

EID: 84962343986     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2009.11.009     Document Type: Article

References (43)

1. Dobosz R., and Zakrzewska A. J. Mol. Struct. (Theochem) 896 (2009) 30-33
2. Woodward R.B., and Hoffman R. J. Am. Chem. Soc. 87 (1965) 2511
3. Kumar A., Jain S.K., and Rastogi R.C. J. Mol. Struct. (Theochem) 678 (2004) 55
4. Dziembowska T., Jagodzinska E., Rozwadowski Z., and Kotfica M. J. Mol. Struct. 598 (2001) 229
5. Angelova S., Enchev V., Markova N., Denkova P., and Kostova K. J. Mol. Struct. (Theochem) 711 (2004) 201
6. Nagy P.I., and Fabian W.M.F. J. Phys. Chem. B 110 (2006) 25026
7. Ladjarafi A., Meghezzi H., and Boucekkine A. J. Mol. Struct. (Theochem) 709 (2004) 12
8. Raszynska E.D., Kosinska W., Osmialowsky B., and Gawinecki R. Chem. Rev. 105 (2005) 3561
9. Mennucci B., Toniolo A., and Tomasi J. J. Phys. Chem. A 105 (2001) 7126
10. Elguero J., Marzin C., Katrizky A.R., and Linda P. The tautomerism of heterocycles (1976), Academic Press, New York
11. Luque F.J., Lopez-Bes J.M., Cemeli J., Aroztegui M., and Orozco M. Theor. Chem. Acc. 96 (1997) 105
12. Huang M.-L., Zou J.-W., Yang D.-Y., Ning B.-Z., Shang Z.-C., and Yu Q.-S. J. Mol. Struct. (Theochem) 589-590 (2002) 321
13. Wang Y.-H., Zou J.-W., Zhang B., Lu X.-Y., Jin H.-X., and Yu Q.-S. J. Mol. Struct. (Theochem) 755 (2005) 31
14. Huang G., Xia Y., and Li Y. J. Mol. Struct (Theochem) 896 (2009) 80
15. Srinivas K., Sitha S., Sridhar B., Jayathirtha Rao V., Bhanuprakash K., and Ravikumar K. Struct. Chem. 17 (2006) 561
16. Schlegel H.B., Gund P., and Fluder E.M. J. Am. Chem. Soc. 104 (1982) 5347
17. Kwiatkowsky J.S. Acta Phys. Pol. A55 (1979) 923
18. Ramirez-Galicia G., Pérez-Caballero G., and Rubio M. J. Mol. Struct. (Theochem) 542 (2001) 1-6
19. Kannan S., and Ranesh R. Polyhedron 25 (2006) 3096
20. Chalaça M.Z., and Figueroa-Villar J.D. J. Mol. Struct. 554 (2000) 225
21. Cindric M., Novak T.K., and Uzarevic K. J. Mol. Struct. 750 (2005) 135
22. Zucolotto Chalaça M., Figueroa-Villar J.D., Ellena J.A., and Castellano E.E. Inorg. Chim. Acta 328 (2002) 45
23. Diaz L.C., Demuner A.J., Valente V.M.M., Barbosa L.C.A., Martins F.T., Doriguetto A.C., and Ellena J.A. J. Agric. Food Chem. 57 (2009) 1399
24. R. Kaoua, Thèse de magistère, U.S.T.H.B., Alger (2005).
25. Armbruster N., Görth M., Klingebiel U., and Schmatz S. J. Organomet. Chem. 693 (2008) 197
26. Andres J., Domingo L.R., Picher M.T., and Safont V.S. Int. J. Quant. Chem. 66 (1998) 9
27. Frau J., Donoso J., Munoz F., and Blanco F.G. J. Mol. Struct. (Theochem) 390 (1997) 255
28. Kless A., Borner A., Heller D., and Selke R. Organometallics 16 (1997) 2096
29. Jabin I., Revial G., Tomas A., Lemoine P., and Pfau M. Tetrahedron: Asymmetry 6 (1995) 1795
30. Lammertsma K., and Prasad B.V. J. Am. Chem. Soc. 116 (1994) 642
31. Cantos A., March P., Moreno-Manas M., Pla A., Sanchez-Ferrando F., and Virgili A. Bull. Chem. Soc. Japan 60 (1987) 4425
32. Zanotti G., Filira F., and Del Pra A. Acta Cryst B34 (1978) 2769
33. Gilli P., Bertolasi V., Ferretti V., and Gilli G. J. Am. Chem. Soc. 122 (2000) 10405
34. Gaussian 03, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M. W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian, Inc., Pittsburgh, PA, 2003.
35. Becke A.D. Phys. Rev. A 38 (1988) 3098
36. Lee C., Yang R.G., and Parr. Phys. Rev. B 37 (1988) 787
37. J. P. Foster, F, J. Weinhold, J. Am. Chem. Soc., 102 (1980) 7211.
38. Machura B., Jaworska M., and Lodowski P. J. Mol. Struct. (Theochem) 766 (2006) 1
39. Miertus S., Scrocco E., and Tomasi J. J. Chem. Phys. 55 (1981) 117
40. Tomasi J., and Persico M. Chem. Rev. 94 (1994) 2027
41. Adamo C., and Barone V. J. Chem. Phys. 108 (1997) 664
42. Reed A.E., Curtiss L.A., and Weinhold F. Chem. Rev. 88 (1988) 899
43. Lu S.-P., and Lewin A.H. Tetrahedron 54 (1998) 15097