Basicity of azoles: Complexes of diiodine with imidazoles, pyrazoles and triazoles

Journal of Physical Organic Chemistry

Volumn 10, Issue 9, 1997, Pages 669-674

  El Ghomari, M J ^a   Mokhlisse, R ^a   Laurence, C ^b   Le Questel, J Y ^b   Berthelot, M ^b  

^a FACULTÉ DES SCIENCES SEMLALIA   (Morocco)

^b UNIVERSITÉ DE NANTES   (France)

Author keywords

Azoles; Basicity; Diiodine complexes

Indexed keywords

EID: 0011778812     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1395(199709)10:9<669::AID-POC933>3.0.CO;2-3     Document Type: Article

References (38)

1. (a) J. Elguero, E. Gonzalez and R. Jacquier, Bull. Soc. Chim. Fr. 5009-5017 (1968);
2. (b) M. Meot-Ner, J. F. Liebman and J. E. Del Bene, J. Org. Chem. 51, 1105-1110 (1986);
3. (c) J. Catalan, J. L. M. Abboud and J. Elguero, Adv. Heterocycl. Chem. 41, 187-274 (1987);
4. (d) J. Catalan, R. M. Claramunt, J. Elguero, J. Laynez, M. Menendez, F. Anvia, J. H. Quian, M. Taagepera and R. W. Taft, J. Am. Chem. Soc. 110, 4105-4111 (1988);
5. (e) L. Z. Chen, R. Flamang, A. Maquestiau, R. W. Taft, J. Catalan, P. Cabildo, R. M. Claramunt and J. Elguero, J. Org. Chem. 56, 179-183 (1991).
6. M. H. Abraham, P. P. Duce, D. V. Prior, D. G. Barratt, J. J. Morris and P. J. Taylor, J. Chem. Soc., Perkin Trans. 2 1355-1375 (1989).
7. G. Guihéneuf, K. Sraïdi, R. Claramunt and J. Elguero, C.R. Acad. Sci., Sér. 2 305, 567-569 (1987).
8. R. G. Pearson, J. Am. Chem. Soc. 107, 6801-6806 (1985).
9. C. Raby, J. F. Lagorce, A. C. Jambut-Absil, J. Buxeraud and G. Catanzano, Endocrinology 126, 1683-1691 (1990).
10. C. Raby, J. Claude, C. Moesch and J. Buxeraud, C.R. Acad. Sci., Sér. C 288, 319-322 (1979).
11. D. S. Cooper, N. Engl. J. Med. 311, 1353-1362 (1984).
12. (a) A. I. Popov, C. C. Bisi and M. Craft, J. Am. Chem. Soc. 80, 6513-6516 (1958);
13. (b) F. M. D'Itri and A. I. Popov, J. Am. Chem. Soc. 90, 6476-6481 (1968);
14. (c) M. Ciureanu and V. E. Sahini, Rev. Roum. Chim. 22, 1441-1446 (1977);
15. (d) P. C. Dwivedi and A. K. Banga, J. Inorg. Nucl. Chem. 42, 1767-1769 (1980);
16. (e) R. A. Mahmoud, A. A. El-Samahy and M. M. Rabia, J. Solution Chem. 13, 517-522 (1984).
17. N. J. Rose and R. S. Drago, J. Am. Chem. Soc. 81, 6138-6145 (1959).
18. Wavefunction, Inc.: 18401 von Karman, #210, Irvine, CA.
19. A. C. Legon, D. G. Lister and J. C. Thorn, J. Chem. Soc., Faraday Trans. 90, 3205-3212 (1994).
20. (a) P. V. Huong, N. Platzer and M. L. Josien, J. Am. Chem. Soc. 91, 3669-3670 (1969);
21. (b) I. Uruska, Spectrochim. Acta, Part A 36, 639-646 (1980);
22. (c) J. Malecki, in Molecular Interactions, edited by H. Ratajczak and W. J. Orville-Thomas, Vol. 3, pp. 183-240, Wiley, New York (1982).
23. G. Aloisi, G. Cauzzo and U. Mazzucato, Trans. Faraday Soc. 63, 1858-1862 (1967).
24. I. Cau, F. Cristiani, F. A. Devillanova and G. Verani, J. Chem. Soc., Perkin Trans 2 749-751 (1985).
25. B. B. Bhowmik and S. P. Chattopadhyay, Spectrochim. Acta, Part A 37, 135-139 (1981).
26. R. P. Lang, J. Am. Chem. Soc. 84, 4438-4441 (1962).
27. J. Oszczapowicz, in The Chemistry of Amidines and Amidates, Vol. 2, edited by S. Patai and Z. Rappoport, pp. 623-688. Wiley, Chichester (1991).
28. E. D. Raczynska, C. Laurence and M. Berthelot, Can. J. Chem. 70, 2203-2208 (1992).
29. U. C. Singh and P. Kollman, J. Phys. Chem. 87, 5386-5388 (1983).
30. H. I. Bloemink and A. C. Legon, J. Chem. Phys. 103, 876-882 (1995).
31. O. Setokuchi and Y. Shimizu, J. Mol. Struct. (Theochem) 281, 67-74 (1993).
32. R. Abdel-Hamid, A. A. El-Samahy, A. H. El-Taher and H. El-Sagher, Can. J. Chem. 65, 468-472 (1987).
33. C. Hansh, A. Leo and R. W. Taft, Chem. Rev. 91, 165-195 (1991).
34. R. W. Taft, in Steric Effects in Organic Chemistry, edited by M. S. Newman, pp. 556-675. Wiley, New York (1956).
35. M. Charton, in Similarity Models in Organic Chemistry and Related Fields, edited by R. I. Zalewski, T. M. Krygowski and J. Shorter, pp. 629-687. Elsevier, Amsterdam (1991).
36. C. Reid and R. S. Mulliken, J. Am. Chem. Soc. 76, 3869-3874 (1954).
37. M. Charton, Top. Curr. Chem. 114, 57-91 (1983).
38. H. Yada, J. Tanaka and S. Nagakurra, Bull. Chem. Soc. Jpn. 33, 1660-1667 (1960).