View PDF Version
 
DOI: 10.1039/A708667I (Paper) Reference Section for: J. Chem. Soc., Dalton Trans., 1998, 881-892

Synthesis, NMR, relaxometry and circularly polarised luminescence studies of macrocyclic monoamidetris(phosphinate) complexes bearing a remote chiral centre

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

Silvio Aime, Mauro Botta, Rachel S. Dickins, Christine L. Maupin, David Parker, James P. Riehl and J. A. Gareth Williams

Abstract

Lanthanide complexes of macrocyclic monoamidetris(phosphinate) ligands are partially hydrated in aqueous solution. Introduction of a chiral centre into the amide group leads to the formation of only two non-interconverting complex diastereoisomers (2∶1 for α-phenylethyl and 4∶1 for α-1-naphthylethyl). Proton, 31P NMR and circularly polarised luminescence studies indicated that the configuration at the chiral carbon centre determines the helicity of the layout of the pendent arms and the macrocyclic ring conformation, with an RRR or SSS configuration preferred at the phosphorus centres.

References

  1. D. Parker and J. A. G. Williams, J. Chem. Soc., Dalton Trans., 1996, 3613 RSC.
  2. S. Aime, M. Botta, D. Parker and J. A. G. Williams, J. Chem. Soc., Dalton Trans., 1995, 2259 RSC.
  3. K. P. Pulukkody, T. J. Norman, D. Parker, L. Royle and C. J. Broan, J. Chem. Soc., Perkin Trans. 2, 1993, 605 RSC.
  4. A. Harrison, T. J. Norman, D. Parker, L. Royle, K. A. Pereira, K. P. Pulukkody and C. A. Walker, Magn. Reson. Imaging, 1993, 11, 761 CrossRef CAS.
  5. S. Aime, M. Botta, D. Parker and J. A. G. Williams, J. Chem. Soc., Dalton Trans., 1996, 17 RSC.
  6. R. S. Dickins, J. A. K. Howard, C. W. Lehmann, J. Moloney, D. Parker and R. D. Peacock, Angew. Chem., Int. Ed. Engl., 1997, 521 CrossRef CAS.
  7. R. S. Dickins, J. A. K. Howard, J. Moloney, D. Parker, R. D. Peacock and G. Siligardi, Chem. Commun., 1997, 1747 RSC.
  8. J.-J. Yaouanc, N. Le Bris, G. Le Gall, J.-C. Clement, H. Handel and H. des Abbayes, J. Chem. Soc., Chem. Commun., 1991, 206 RSC.
  9. E. Cole, C. J. Broan, K. J. Jankowski, P. K. Pulukkody, D. Parker, A. T. Millican, N. R. A. Beeley, K. Millar and B. A. Boyce, Synthesis, 1992, 67.
  10. I. Bertini and C. Luchinat, NMR of Paramagnetic Molecules in Biological Systems, Benjamin-Cummings, Boston, MA, 1986 Search PubMed.
  11. T. J. Swift, in NMR of Paramagnetic Molecules: Principles and Applications, eds. G. N. LaMar, W. De W. Horrocks and R. H. Holm, Academic Press, London, 1973 Search PubMed.
  12. S. Aime, A. S. Batsanov, M. Botta, 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 RSC.
  13. S. Aime, A. S. Batsanov, M. Botta, J. A. K. Howard, D. Parker, P. K. Senanayake and J. A. G. Williams, Inorg. Chem., 1994, 33, 4696 CrossRef CAS.
  14. S. Aime, M. Botta and G. Ermondi, Inorg. Chem., 1992, 32, 4296.
  15. S. Aime, M. Botta, M. Fasano and E. Terreno, Chem. Soc. Rev., 1998, 27, 19 RSC; R. B. Lauffer, Chem. Rev., 1987, 87, 901 CrossRef CAS.
  16. J. F. Desreux, Inorg. Chem., 1980, 19, 1319 CrossRef CAS; X. Wang, T. Jin, V. Comblin, A. Lopez-Mut, E. Merciny and J. F. Desreux, Inorg. Chem., 1992, 31, 1095 CrossRef CAS.
  17. J.-P. Dubost, M. Leger, M. H. Langlois, D. Meyer and M. C. Schaefer, C. R. Acad. Sci., Ser. 2, 1991, 312, 349 Search PubMed.
  18. J. A. Peters, J. Huskens and D. J. Raber, Prog. Nucl. Magn. Reson. Spectrosc., 1996, 18, 283 CrossRef CAS.
  19. S. Aime, M. Botta, M. Grandi, M. Panero and F. Uggeri, Magn. Reson. Chem., 1991, 29, 293.
  20. K. A. Connors, in Comprehensive Supramolecular Chemistry, eds. J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vogtle and J.-M. Lehn, Pergamon, Oxford, 1996, vol. 3, ch. 6 Search PubMed.
  21. A. Beeby, D. Parker and J. A. G. Williams, J. Chem. Soc., Perkin Trans. 2, 1996, 1165 Search PubMed; D. Parker and J. A. G. Williams, J. Chem. Soc., Perkin Trans. 2, 1996, 1581 RSC.
  22. D. Parker and J. A. G. Williams, J. Chem. Soc., Perkin Trans. 2, 1995, 1305 RSC.
  23. R. S. Dickins, D. Parker, A. S. deSousa and J. A. G. Williams, Chem. Commun., 1996, 697 RSC.
  24. D. T. Richens, The Chemistry of Aqua Ions, Wiley, Chichester, 1997, ch. 3 Search PubMed.
  25. J. P. Riehl and F. S. Richardson, Methods Enzymol., 1993, 226, 539 CAS.
  26. D. H. Metcalf, S. W. Snyder, J. N. DeMar and F. S. Richardson, J. Am. Chem. Soc., 1990, 112, 469 CrossRef CAS.
  27. E. Huskowska, C. L. Maupin, D. Parker, J. P. Riehl and J. A. G. Williams, Enantiomer, 1998, in the press Search PubMed.
  28. Y. Haas and G. Stein, J. Chem. Phys., 1971, 75, 3668 CAS.
  29. K. Nakamura, Bull. Chem. Soc. Jpn., 1982, 55, 2697 CAS.
  30. S. R. Meech and D. Phillips, J. Photochem., 1983, 23, 193 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.