Ground- and excited-state properties of some naphthoflavyliums

Canadian Journal of Chemistry

Volumn 74, Issue 5, 1996, Pages 697-706

  Elhabiri, Mourad ^a   Figueiredo, Paulo ^a   George, Florian ^a   Cornard, Jean Paul ^b   Fougerousse, André ^a   Merlin, Jean Claude ^b   Brouillard, Raymond ^a  

^a UNIVERSITÉ LOUIS PASTEUR   (France)

^b UNIVERSITÉ DES SCIENCES ET TECHNOLOGIES DE LILLE   (France)

Author keywords

Fluorescence; Hydration and deprotonation constants; Metallic complexation; Molecular orbital calculations; Naphthoflavylium synthesis

Indexed keywords

COMPLEXATION; FLUORESCENCE; HYDRATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS (CHEMICAL);

DEPROTONATION CONSTANTS; MOLECULAR ORBITAL CALCULATIONS; NAPHTHOFLAVYLIUMS;

SALTS;

EID: 0030149916     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-075     Document Type: Article

References (52)

1. T. Goto and T. Kondo. Angew. Chem. Int. Ed. Engl. 30, 17 (1991).
2. R. Brouillard and O. Dangles. In The flavonoids, advances in research since 1986. Edited by J.B. Harborne. Chapman and Hall, London. 1993. pp. 565-588.
3. J.B. Harborne and R.J. Grayer. In The flavonoids, advances in research since 1980. Edited by J.B. Harborne. Chapman and Hall, London. 1988. pp. 1-20.
4. J.J. Macheix and A. Fleuriet. In Polyphenolic phenomena. Edited by A. Scalbert. INRA Editions, Versailles. 1993. pp. 157-163.
5. F.J. Francis. In Polyphenolic phenomena. Edited by A. Scalbert. INRA Editions, Versailles. 1993. pp. 209-220.
6. R. Brouillard and J.E. Dubois. J. Am. Chem. Soc. 99, 1359 (1977).
7. R. Brouillard and B. Delaporte. J. Am. Chem. Soc. 99, 8461 (1977).
8. R. Brouillard, B. Delaporte, and J.E. Dubois. J. Am. Chem. Soc. 100, 6202 (1978).
9. P. Furtado, P. Figueiredo, H.C. Neves, and F. Pina. J. Photochem. Photobiol. A: 75, 113 (1993).
10. P. Figueiredo. Ph.D. Thesis. Universidade Nova de Lisboa (1994).
11. R. Brouillard. Phytochemistry, 22, 1311 (1983).
12. R. Brouillard, G. Mazza, Z. Saad, A.M. Albrecht-Gary, and A. Cheminat. J. Am. Chem. Soc. 111, 2604 (1989).
13. T. Hoshino and T. Goto. Tetrahedron Lett. 31, 1593 (1990).
14. G. Mazza and R. Brouillard. Phytochemistry, 29, 1097 (1990).
15. P. Rüedi and B. Hutter-Beda. Bull. Liaison - Groupe Polyphenols, 15, 332 (1990).
16. Y. Cai, T.H. Lilley, and E. Haslam. J. Chem. Soc. Chem. Commun. 380 (1990).
17. T.V. Mistry, Y. Cai, T.H. Lilley, and E. Haslam. J. Chem. Soc. Perkin Trans. 2, 1287 (1991).
18. O. Dangles and R. Brouillard. Can. J. Chem. 70, 2174 (1992).
19. O. Dangles and R. Brouillard. J. Chem. Soc. Perkin Trans. 2, 247 (1992).
20. O. Dangles, N. Saito, and R. Brouillard. Phytochemistry, 34, 119 (1993).
21. O. Dangles, N. Saito, and R. Brouillard. J. Am. Chem. Soc. 115, 3125 (1993).
22. O. Dangles, M. Elhabiri, and R. Brouillard. J. Chem. Soc. Perkin Trans. 2, 2587 (1994).
23. P. Figueiredo, M. Elhabiri, K. Toki, N. Saito, O. Dangles, and R. Brouillard. Phytochemistry, 41, 301 (1996).
24. G.A. Iacobucci and J.G. Sweeny. Tetrahedron, 39, 3005 (1983).
25. G. Hauke, P. Czerney, C. Igney, and H. Hartmann. Ber. Bunsen-Ges. Phys. Chem. 93, 805 (1989).
26. J. Baranac, D. Amić, and V. Vukanović. J. Agric. Food Chem. 38, 932 (1990).
27. D. Amić, J. Baranac, and V. Vukanović. J. Agric. Food Chem. 38, 936 (1990).
28. D. Amić and J. Baranac. Croat. Chem. Acta, 64, 27 (1991).
29. G. Rastelli, L. Costantino, and A. Albasini. J. Mol. Struct. 279, 157 (1993).
30. O. Dangles, and H. Elhajji. Helv. Chim. Acta, 77, 1595 (1994).
31. D. Davidović-Amić, D. Amić, and N. Trinajstić. Croat. Chem. Acta, 67, 163 (1994).
32. L. Jurd. Tetrahedron, 25, 2367 (1969).
33. M.C. Wigand, O. Dangles, and R. Brouillard. Phytochemistry, 31, 4317 (1992).
34. P. Figueiredo, J.C. Lima, H. Santos, M.C. Wigand, R. Brouillard, A.L. Maçanita, and F. Pina. J. Am. Chem. Soc. 116, 1249 (1994).
35. R.A. McClelland, D.B. Devine, and P.E. Sorensen. J. Am. Chem. Soc. 107, 5459 (1985).
36. R. Brouillard and J. Lang. Can. J. Chem. 68, 755 (1990).
37. P. Figueiredo, F. Pina, L. Vilas-Boas, and A.L. Maçanita. J. Photochem. Photobiol. A: 52, 411 (1990).
38. J.C. Lima, P. Danesh, P. Figueiredo, F.S. Pina, and A. Maçanita. Photochem. Photobiol. 59, 412 (1994).
39. E.S. Sadlowski. Ph.D. Thesis, Colorado State University, Fort Collins, Colo. 1985.
40. K. Takeda, Y. Yamashita, A. Takahashi, and C.F. Timberlake. Phytochemistry, 29, 1089 (1990).
41. T. Kondo, K. Yoshida, A. Nakagawa, T. Kawai, H. Tamura, and T. Goto. Nature (London), 358, 515 (1992).
42. N. Filipescu, S.K. Chakrabarti, and P.G. Tarassoff. J. Phys. Chem. 77, 2276 (1973).
43. S. Tripathi, M. Simalty, and J. Kossanyi. Tetrahedron Lett. 26, 1995 (1985).
44. V. Wintgens, S. Tripathi, J. Pouliquen, and J. Kossanyi. J. Photochem. 32, 81 (1986).
45. C. Reichardt. Angew. Chem. Int. Ed. Engl. 4, 29 (1965).
46. H. Santos, D.L. Turner, J.C. Lima, P. Figueiredo, F. Pina, and A.L. Maçanita. Phytochemistry, 33, 1227 (1993).
47. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart. J. Am. Chem. Soc. 107, 3902 (1985).
48. W.E. Hull. In Two-dimensional NMR spectroscopy: applications for chemists and biochemists. Edited by W.R. Croasmun and R.M.K. Carlson. VCH Publishers, New York. 1987.
49. W.P. Aue, E. Bartoldi, and R.R. Ernst. J. Chem. Phys. 71, 4546 (1979).
50. A. Bax and R. Freeman. J. Magn. Reson. 44, 542 (1981).
51. A. Statoua, J.C. Merlin, R. Brouillard, and M. Delhaye. C.R. Acad. Sci. Paris, 296, 1397 (1983).
52. J. Andrieux, B. Bodo, and D. Molho. Bull. Soc. Chim. Fr. 3421 (1973).