Synthesis of new heterotridentate ligands comprising mixed hard–soft donor sets, and their complexation with Group 10 metals

(Note: The full text of this document is currently only available in the PDF Version )

Pravat Bhattacharyya, Jonathan Parr and Alexandra M. Z. Slawin


Abstract

The new phosphorus-containing heterotridentate ligands 2-(2-Ph2P)C6H4CH[double bond, length half m-dash]NCH(Me)CH(OH)Ph-1S,2R (HL1) and 2-(2-Ph2P)C6H4N[double bond, length half m-dash]CHC6H4OH (HL2) were prepared by the condensation of 2-(diphenylphosphino)benzaldehyde with 1S,2R-norephedrine (HL1) and 2-(diphenylphosphino)aniline with salicylaldehyde (HL2). The co-ordination chemistry of HL1 and HL2 with Group 10 metals was explored, together with that of the previously reported ligand 2-(2-Ph2P)C6H4CH[double bond, length half m-dash]NC6H4OH (HL3) which is isomeric with (HL2). Compound HL1 affords cationic complexes of general formula [M(HL1)Cl]Cl, where M = Ni (1), Pd (2) or Pt (3). Spectroscopic, microanalytical and crystallographic data for 1–3 confirm that deprotonation of the hydroxyl group does not occur on complexation. In contrast, both HL2 and HL3 deprotonate on complexation to form neutral species of general formula [MLCl] where L = L2, M = Ni (4), Pd (5) or Pt (6); L = L3, M = Ni (7), Pd (8) or Pt (9). The crystal structures of 4, 5, 7 and 9 confirm tridentate PNO co-ordination of the deprotonated ligands to the metal centres, forming 5- and 6-membered rings.


References

  1. See, for example, (a) G. R. Newkome, Chem. Rev., 1993, 93, 2067 CrossRef CAS; (b) A. Bader and E. Lindner, Coord. Chem. Rev., 1991, 108, 27 CrossRef CAS; (c) K. L. Bray, C. P. Butts, G. C. Lloyd-Jones and M. Murray, J. Chem. Soc., Dalton Trans., 1998, 1421 RSC; (d) R. W. Wegman, A. G. Abatjoglou and A. M. Harrison, J. Chem. Soc., Chem. Commun., 1987, 1891 RSC; (e) W. H. Chan, Z. Z. Zhang, T. C. W. Mak and C. M. Che, J. Chem. Soc., Dalton Trans., 1998, 803 RSC; (f) G. Francio, R. Scopelliti, C. G. Arena, G. Bruno, D. Drommi and F. Faraone, Organometallics, 1998, 17, 338 CrossRef CAS; (g) C. A. Ghilardi, S. Midollini, S. Moneti, A. Orlandini and G. Scappaci, J. Chem. Soc., Dalton Trans., 1992, 3371 RSC; (h) A. Del Zotto, G. Nardin and P. Rigo, J. Chem. Soc., Dalton Trans., 1995, 3343 RSC; (i) H. Brunner and A. F. M. M. Rahman, Chem. Ber., 1984, 117, 710 CAS.
  2. H. J. Banbery, W. Hussain, T. A. Hamer, C. J. Jones and J. McCleverty, J. Chem. Soc., Dalton Trans., 1990, 657 RSC.
  3. K. K. Hii, S. D. Perera and B. L. Shaw, J. Chem. Soc., Dalton Trans., 1994, 3589 RSC.
  4. K. Mashima, Y. Kaneda, A. Fukumoto, M. Tanaka, K. Tani, H. Nakamo and A. Nakamura, Inorg. Chim. Acta, 1998, 270, 459 CrossRef CAS.
  5. J. Andrieu, B. R. Steele, C. G. Sorettas and C. J. Cardin, Organometallics, 1998, 17, 839 CrossRef CAS.
  6. J. R. Dilworth, S. D. Howe, A. J. Hutson, J. R. Miller, J. Silver, R. M. Thompson, M. Harman and M. B. Hursthouse, J. Chem. Soc., Dalton Trans., 1994, 3553 RSC.
  7. K. Tani, M. Yakuta, S. Nakamura and T. Yamagata, J. Chem. Soc., Dalton Trans., 1993, 2781 RSC.
  8. Y. Kataoka, Y. Tsuji, O. Matsumoto, M. Ohashi, T. Yamagata and K. Tani, J. Chem. Soc., Chem. Commun., 1995, 2099 RSC.
  9. H. Yang, M. Alvarez, N. Lugan and R. Mathieu, J. Chem. Soc., Chem. Commun., 1995, 1721 RSC.
  10. H. Yang, M. Alvarez Gressier, N. Lugan and R. Mathieu, Organometallics, 1997, 16, 140.
  11. H. A. Ankersmit, N. Veldman, A. L. Spek, K. Vrieze and G. Van Koten, Inorg. Chim. Acta, 1996, 252, 339 CrossRef CAS.
  12. P. Wehman, R. E. Rulke, V. E. Kaasjager, P. C. J. Kamer, H. Kooijman, A. L. Spek, C. J. Elsevier, K. Vrieze and P. W. N. M. Van Leeuwen, J. Chem. Soc., Chem. Commun., 1995, 331 RSC.
  13. S. D. Perera, M. Shamsuddin and B. L. Shaw, Can. J. Chem., 1995, 73, 1010 CAS.
  14. N. Gündüz, T. Gündüz, M. B. Hursthouse, H. G. Parkes, L. S. Shaw (née Gözen), R. A. Shaw and M. Tüzün, J. Chem. Soc., Perkin Trans. 2, 1985, 899 RSC.
  15. J. Chatt, L. M. Vallerino and L. M. Venanzi, J. Chem. Soc., 1957, 2496 RSC.
  16. M. K. Cooper, J. M. Downes, P. A. Duckworth and E. R. T. Tiekink, Aust. J. Chem., 1992, 45, 595 CAS.
  17. G. M. Sheldrick, SHELXTL, version 5.03, program for crystal structure solution, University of Göttingen, 1994.
  18. TEXSAN, Crystal Structure Analysis Package, Molecular Structures Corporation, The Woodlands, TX, 1985 and 1992.
  19. DIFABS, N. G. Walker and D. Stuart, Acta Crystallogr., Sect. A, 1983, 39, 158 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.