Dimethylthiophosphoryl hydrazone ligands and their copper complexes: crystal structures and analysis of their solution complexation behaviour by electrospray mass spectrometry

Abstract

Four new thiophosphoryl ligands containing NNPS or CNPS connectivities have been prepared and three of them characterised by single-crystal X-ray diffraction. The complexation of these ligands with salts of Cu^I, Cu^II, Ni^II and Zn^II has been studied by electrospray mass spectrometry and uv-visible spectrophotometry in acetonitrile and methanol solution. Evidence for 1∶1 and 2∶1 complexation is presented. Two copper(I) complexes were isolated including a mixed chloride–bromide copper(I) complex in which a dimeric structure is adopted with a 22-membered metallacycle.

References

1. K. V. Katti, V. S. Reddy and P. R. Singh, Chem. Soc. Rev., 1995, 97.
2. W. A. Volkert, P. R. Singh, A. R. Ketring, K. V. Katti and K. K. Katti, J. Labelled Compd. Radiopharm., 1993, 32, 15.
3. K. V. Katti, P. R. Singh and C. L. Barnes, Inorg. Chem., 1992, 31, 4588.
4. A. Schmidtpeter and J. Ebeling, Chem. Ber., 1968, 101, 815; R. Bohm, H. Groeger and H. Schmidtpeter, Angew. Chem., 1964, 76, 860; E. Fluck and F. L. Goldman, Chem. Ber., 1963, 96, 3091.
5. M. R. Churchill and J. Wormald, Chem. Commun., 1970, 703; A. Davison and E. S. Switkes, Inorg. Chem., 1971, 10, 837; M. R. Churchill, J. Cooke, J. Wormald, A. Davison and E. S. Switkes, J. Am. Chem. Soc., 1969, 91, 6518.
6. S. Aime, M. Botta, A. S. Batsanov, R. S. Dickins, S. Faulkner, C. E. Foster, A. Harrison, J. A. K. Howard, J. M. Moloney, T. J. Norman, D. Parker, L. Royle and J. A. G. Williams, J. Chem. Soc., Dalton Trans., 1997, 3623; C. D. Edlin and D. Parker, Tetrahedron Lett., 1998, 2797; G. B. Bates, E. Cole, R. Kataky and D. Parker, J. Chem. Soc., Dalton Trans., 1996, 2693; T. Kiss, M. Jezowrska-Bojezuk, H. Kozlowski, P. Kosfarski and A. Antozak, J. Chem. Soc., Dalton Trans., 1991, 2275.
7. M. A. M. Easson and D. Parker, Tetrahedron Lett., 1997, 6091.
8. J. K. Lion, C. J. Mathias and M. A. Green, J. Med. Chem., 1997, 40, 132; Y. Fujibayashi, H. Taniuchi, Y. Yanekura, H. Ohtani, J. Konishi and A. Yokayama, J. Nucl. Med., 1997, 38, 1155.
9. H. Reinhardt, D. Bianchi and D. Molle, Chem. Ber., 1957, 1656.
10. W. Kuchen and H. Buchwald, Angew. Chem., 1959, 4, 162.
11. A. C. Cope, D. S. Smith and R. J. Cotter, Org. Synth., 1963, Coll. Vol. IV, 377.
12. H. Schlesinger, Angew. Chem., 1960, 5, 563.
13. R. S. Rowland and R. Taylor, J. Phys. Chem., 1996, 100, 7384.
14. F. H. Allen, C. M. Bird, R. S. Rowland and P. R. Raithby, Acta Crystallogr., Sect. B, 1997, 53, 680.
15. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1.
16. C. Silvestru, R. Röster, I. Haiduc, R. Cea-Olivares and G. Espinosa-Perez, Inorg. Chem., 1995, 34, 3352; D. Cupertino, R. Keyte, A. M. Z. Slawin, D. J. Williams and J. D. Woollins, Inorg. Chem., 1996, 35, 2695; N. S. Hosmane, A. M. Arif and A. H. Cowley, Acta Crystallogr., Sect. C, 1987, 43, 2013.
17. J. B. Fenn, M. Mann, C. K. Meng, S. F. Wong and C. M. Whitehouse, Science, 1989, 246, 64.
18. G. Hopfgartner, C. Piquet, J. D. Henion and A. F. Williams, Helv. Chim. Acta, 1993, 76, 1759.
19. E. Leize, A. Jaffrezic and A. Van Dorsellaer, J. Mass Spectrom., 1996, 31, 537.
20. M. Goodall, P. M. Kelly, D. Parker, K. Gloe and H. Stephan, J. Chem. Soc., Perkin Trans. 2, 1997, 59.
21. B. Delavaux-Nicot, N. Lugan, R. Mathieu and J.-P. Majoral, Inorg. Chem., 1992, 31, 334.
22. A. Schmidtpeter, J. Gross, E. Schrenk and W. S. Sheldrick, Phosphorus Sulphur Relat. Elem., 1982, 14, 49; B. Wallis, C. Donath, M. Meisel and J. Fuchs, Acta Crystallogr., Sect. C, 1991, 47, 2423; G. L'Abbe, J. Flemal, J. P. Declercq, G. Germain and M. van Meerssche, Bull. Soc. Chim. Belg., 1979, 88, 737.
23. T. Steiner, Acta Crystallogr., Sect. B, 1998, 54, 456.
24. S. Wolfe, Can. J. Chem., 1971, 49, 1099.
25. G. M. Sheldrick, SHELXTL, Version 5/VMS, Bruker axs, Analytical X-ray systems, Madison, WI, 1995.
26. G. M. Sheldrick, SADABS, Program for scaling and correction of area detector data, University of Göttingen, 1996.