Supramolecular Polymers and Chiral Phosphine Oxides by Oxidation of Gold(I) Complexes

  • Nasser Nasser
  • Richard J. Puddephatt


The chiral diphosphine ligand R,R-cyclo-C6H10-trans-1,2-{NHC(=O)C6H4-2-PPh2}2, 1, forms complexes with gold(I) of formula [Au(1)]Cl, 2, and [(ClAu)2(µ-1)], 3, in which the diphosphine acts as a trans-chelate and bridging ligand, respectively. Oxidation of these gold(I) complexes leads to dissociation and oxidation of the diphosphine ligand to form the corresponding diphosphine dioxide R,R-cyclo-C6H10-1,2-{NHC(=O)C6H4-2-P(=O)Ph2}2, which has been crystallized in its protonated form and as complexes with Na+ and Fe2+, with [AuBr2] or [AuBr4] anions. Some of these compounds form supramolecular polymers by intermolecular hydrogen bonding.


Gold Bis(phosphine oxide) Diphosphine Supramolecular Polymer 



We thank the NSERC (Canada) for financial support and A. Borecki, B. Cooper and M. Jennings for expert assistance with the structure determinations.

Supplementary material

10904_2017_577_MOESM1_ESM.cif (294 kb)
Supplementary material 1 (CIF 294 KB)


  1. 1.
    P. Stepnicka, Chem. Soc. Rev. 41, 4273 (2012)CrossRefGoogle Scholar
  2. 2.
    B.M. Trost, D.L. van Vranken, Angew. Chem. Int. Ed. 31, 228 (1992)CrossRefGoogle Scholar
  3. 3.
    B.M. Trost, F.D. Toste, J. Am. Chem. Soc. 121, 4545 (1999)CrossRefGoogle Scholar
  4. 4.
    C.P. Butts, E. Filali, G.C. Lloyd-Jones, P.-O. Norrby, D.A. Sale, Y. Schramm, J. Am. Chem. Soc. 137, 9945 (2009)CrossRefGoogle Scholar
  5. 5.
    N. Nasser, R.J. Puddephatt, Chem. Commun. 47, 2808 (2011)CrossRefGoogle Scholar
  6. 6.
    N. Nasser, P.D. Boyle, R.J. Puddephatt, J. Organomet. Chem. 784, 88 (2015)CrossRefGoogle Scholar
  7. 7.
    N. Nasser, R.J. Puddephatt, Polyhedron 69, 61 (2014)CrossRefGoogle Scholar
  8. 8.
    N. Nasser, R.J. Puddephatt, Inorg. Chim. Acta 409, 238 (2014)CrossRefGoogle Scholar
  9. 9.
    N. Nasser, P.D. Boyle, R.J. Puddephatt, Organometallics 32, 5504 (2013)CrossRefGoogle Scholar
  10. 10.
    N. Nasser, A. Borecki, P.D. Boyle, R.J. Puddephatt, Inorg. Chem. 52, 7051 (2013)CrossRefGoogle Scholar
  11. 11.
    N. Nasser, R.J. Puddephatt, Cryst. Growth Des. 12, 4275 (2012)CrossRefGoogle Scholar
  12. 12.
    N. Nasser, D.J. Eisler, R.J. Puddephatt, Chem. Commun. 46, 1953 (2010)CrossRefGoogle Scholar
  13. 13.
    R.A. Swanson, B.O. Patrick, M.J. Ferguson, C.J.A. Daley, Inorg. Chim. Acta 360, 2455 (2007)CrossRefGoogle Scholar
  14. 14.
    C. Amatore, A. Jutand, L. Mensah, L. Ricard, J. Organomet. Chem. 692, 1457 (2007)CrossRefGoogle Scholar
  15. 15.
    G.R. Ferrell, C. Moore, A.L. Rheingold, C.J.A. Daley, Acta Cryst E, 65, m1512 (2009)CrossRefGoogle Scholar
  16. 16.
    S. Tasan, C. Licona, P.-E. Doulain, C. Michelin, C.P. Gros, P. Le Gendre, P.D. Harvey, C. Paul, C. Gaiddon, E. Bodio, J. Biol. Inorg. Chem. 20, 143 (2015)CrossRefGoogle Scholar
  17. 17.
    D. Perrault, M. Drouin, A. Michel, P.D. Harvey, Inorg. Chem. 30, 2 (1991)CrossRefGoogle Scholar
  18. 18.
    K. Ariga, V. Malgras, Q. Ji, M.B. Zakaria, Y. Yamauchi, Coord. Chem. Rev. 320, 139 (2016)CrossRefGoogle Scholar
  19. 19.
    B. Li, M. Chrzanowski, Y. Zhang, S. Ma, Coord. Chem. Rev. 307, 106 (2016)CrossRefGoogle Scholar
  20. 20.
    G.N. Pandian, H. Sugiyama, Bull. Chem. Soc. Jpn. 89, 843 (2016)CrossRefGoogle Scholar
  21. 21.
    W.J. Hunks, M.A. MacDonald, M.C. Jennings, R.J. Puddephatt, Organometallics 19, 5063 (2000)CrossRefGoogle Scholar
  22. 22.
    P. Braunstein, R.J.H. Clark, J. Chem. Soc. Dalton Trans. 1845 (1973)Google Scholar
  23. 23.
    J. Suarez-Varela, J.-P. Legros, J. Galy, E. Colacio, J. Ruiz, J.D. Lopez-Gonzalez, P. Leon, R. Perona, Inorg. Chim. Acta 161, 199 (1989)CrossRefGoogle Scholar
  24. 24.
    R.J. Puddephatt, The Chemistry of Gold (Elsevier, New York, 1978)Google Scholar
  25. 25.
    C. Hahn, L. Cruz, A. Villalobos, L. Garza, S. Adeosun, Dalton Trans. 43, 16300 (2014)CrossRefGoogle Scholar
  26. 26.
    A. Vanitcha, G. Gontard, N. Vanthuyne, E. Derat, V. Mouries-Mansuy, L. Fensterbank, Adv. Synth. Catal. 357, 2213 (2015)CrossRefGoogle Scholar
  27. 27.
    E.J. Derrah, C. Martin, S. Ladeira, K. Miqueu, G. Bouhadir, D. Bourissou, Dalton Trans. 41, 14274 (2012)CrossRefGoogle Scholar
  28. 28.
    C.F. Shaw, A.A. Isab, J.D. Hoeschele, M. Starich, J. Locke, P. Schulties, J. Xiao, J. Am. Chem. Soc. 116, 2254 (1994)CrossRefGoogle Scholar
  29. 29.
    F.J. Alguacil, C. Caravaca, S. Martinez, A. Cobo, Hydrometallurgy 36, 369 (1994)CrossRefGoogle Scholar
  30. 30.
    APEX 2, Crystallography Software Package. (Bruker AXS, Madison, 2005)Google Scholar
  31. 31.
    SAINT, Data Reduction Software. (Bruker AXS, Madison, 1999)Google Scholar
  32. 32.
    G.M. Sheldrick, SADABS v.2.01, Area Detector Absorption Correction Program. (Bruker AXS, Madison, 2006)Google Scholar
  33. 33.
    G.M. Sheldrick, SHELXS, program for solution of crystal structures. Acta Cryst. A64, 112, 2008CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2017

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of Western OntarioLondonCanada

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