Ligand behaviour and reactivity of phenyl 2-pyridyl ketone azine. Structures of two polymorphic forms of the azine and a copper complex of the 3-phenyltriazolo[1,5-a]pyridine *

Abstract

Two polymorphic forms of phenyl 2-pyridyl ketone azine (L¹) and the complex [ZnL¹Cl₂] have been synthesized and characterized by X-ray diffraction analysis. In the reaction with copper(II) chloride both isomers of the azine undergo hydrolytic and oxidative processes, giving rise to the complex [CuL²₂Cl₂] (L² = 3-phenyltriazolo[1,5-a]pyridine). In order to clarify this process, phenyl 2-pyridyl hydrazone (L³) has been synthesized and treated with copper(II) chloride; in this way CuL²(Cl)·H₂O and CuL³Cl₂ were isolated.

References

1. X. Xu, X. You, Z. Sun, X. Wang and H. Liu, Acta Crystallogr., Sect. C, 1994, 50, 1169.
2. R. Bauer and Ch. O. Rupe, Anal. Chem., 1971, 43, 421.
3. G. Shiahuy Chen, J. K. Wilbur, Ch. L. Barnes and R. Glaser, J. Chem. Soc., Perkin Trans. 2, 1995, 2311.
4. V. L. Goedken, Y. Park, S. M. Peng and J. M. Norris, J. Am. Chem. Soc., 1974, 96, 7693; C. Thilgen and F. Vögtle, Chem. Ber., 1991, 124, 671; Th. W. Bell and A. T. Papoulis, Angew. Chem., Int. Ed. Engl., 1992, 31, 749.
5. P. Espinet, J. Etxebarria, M. Marcos, J. Pérez, A. Remon and J. L. Serrano, Angew. Chem., Int. Ed. Engl., 1989, 28, 1065.
6. H. Warren Smith, Acta Crystallogr., Sect. B, 1975, 31, 2701.
7. Ch. J. O'Connor, R. J. Romananch, D. M. Robertson, E. E. Eduok and F. R. Fronczek, Inorg. Chem., 1983, 22, 449.
8. W. J. Stratton, Inorg. Chem., 1970, 9, 517 and refs. therein; P. D. W. Boyd, M. Gerloch and G. M. Sheldrick, J. Chem. Soc., Dalton Trans., 1974, 1097.
9. I. Bertini, Ch. Owens, C. Luchinat and R. S. Drago, J. Am. Chem. Soc., 1987, 109, 5208.
10. L. P. Battaglia, M. Carcelli, F. Ferraro, L. Mavilla, C. Pelizzi and G. Pelizzi, J. Chem. Soc., Dalton Trans., 1994, 2651.
11. C. Amari, C. Pelizzi, G. Predieri, S. Destri and W. Porzio, Synth. Met., 1995, 72, 7.
12. J. Bernstein and A. T. Hagher, J. Am. Chem. Soc., 1978, 100, 673.
13. G. S. Chen, M. Anthamatten, Ch. L. Barnes and R. Glaser, Angew. Chem., Int. Ed. Engl., 1994, 33, 1081.
14. E. C. K. Lai, D. Mackay, N. J. Taylor and K. N. Watson, Can. J. Chem., 1988, 66, 2839.
15. I. Fleming and J. Harley-Mason, J. Chem. Soc., 1961, 5560.
16. T. Ishida, M. Inoue, K. Nasu and T. Kurihara, Acta Crystallogr., Sect. C, 1983, 39, 470.
17. C. K. Johnson, ORTEP II, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN, 1976.
18. R. Glaser, G. Shiahuy Chen and Ch. Barnes, J. Org. Chem., 1993, 58, 7446.
19. F. Grases, F. Garcia-Sanchez and M. Valcarcel, Anal. Chim. Acta, 1981, 125, 21; H. Mori, K. Sakamoto, S. Mashito, Y. Matsouka, M. Matsubayashi and K. Sakai, Chem. Pharm. Bull., 1993, 41, 1944.
20. H. Mori, K. Sakai, K. Yamashina, S. Hirata and K. Horie, Bull. Chem. Soc. Jpn., 1991, 64, 3634.
21. E. Escrivà, J. Server-Carrió, L. Lezama, J. V. Folgado, J. L. Pizarro, R. Ballesteros and B. Abarca, J. Chem. Soc., Dalton Trans., 1997, 2033.
22. G. Valle, R. Ettorre and V. Peruzzo, Acta Crystallogr., Sect. C, 1995, 51, 1293.
23. K. J. Oliver, T. N. Waters, D. F. Cook and C. E. F. Rickard, Inorg. Chim. Acta, 1977, 24, 85.
24. R. C. Stoufer and D. H. Busch, J. Am. Chem. Soc., 1956, 78, 6016.
25. D. Demertzi and D. Nicholls, Inorg. Chim. Acta., 1983, 73, 37.
26. SPARTAN User's guide, Wavefunction Inc., Irvine, CA, 1996.
27. M. S. Lehmann and F. K. Larsen, Acta Crystallogr., Sect. A, 1983, 39, 158.
28. G. M. Sheldrick, SHELXS 86, Program for the solution of crystal structures, University of Göttingen, 1985.
29. A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, G. Giacovazzo, A. Guagliardi and G. Polidori, J. Appl. Crystallogr., 1994, 27, 435.
30. G. M. Sheldrick, SHELX 76, Program for crystal structure determination, University of Cambridge, 1976.
31. M. Nardelli, Comput. Chem., 1983, 7, 95.
32. W. D. S. Motherwell and W. Clegg, PLUTO, Program for plotting molecular and crystal structure, University of Cambridge, 1976.