Structural Chemistry

, Volume 12, Issue 6, pp 459–464 | Cite as

A Theoretical and Experimental Study of the Interaction of C6F6 with Electron Donors

  • Ibon Alkorta
  • Isabel Rozas
  • María Luisa Jimeno
  • José Elguero

Abstract

The NMR effects produced on the nitrogen absolute shieldings in a series of electron donors when they interact with hexafluorobenzene, C6F6, have been theoretically studied. The complexes have been optimized at the B3LYP/6-311++G** level and the NMR shieldings have been calculated using the GIAO method. The results obtained have allowed devising an experiment (C6F6···NCCH3 complex) that is compatible with the theoretical calculations.

Ab initio GIAO calculations nuclear magnetic shieldings intermolecular interactions aromaticity NICS 

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REFERENCES

  1. 1.
    Alkorta, I.; Rozas, I.; Elguero. J. J. Org. Chem. 1997, 62, 4687.Google Scholar
  2. 2.
    Danten, Y.; Tassaing, T.; Besnard, M. J. Phys. Chem. A, 1999, 103, 3530.Google Scholar
  3. 3.
    Gallivan, J. P.; Dougherty, D. A. Org. Lett. 1999, 1, 103.Google Scholar
  4. 4.
    Alkorta, I.; Elguero, J. New. J. Chem. 1998, 22, 381.Google Scholar
  5. 5.
    Schneider, H. J.; Rudiger, V.; Cuber, U. J. Org. Chem. 1995, 60, 996; Abraham, R. J.; Canton, M.; Reid, M.; Griffiths, L. J. Chem. Soc. Perkin Trans. 2, 2000, 803.Google Scholar
  6. 6.
    Martin, N. H.; Allen, N. W.; Minga, E. K.; Ingrassia, S. T.; Brown, J. D. J. Amer. Chem. Soc. 1998, 120, 11510; Martin, N. H.; Allen, N. W.; Minga, E. K.; Ingrassia, S. T.; Brown, J. D. Struct. Chem. 1999, 10, 375.Google Scholar
  7. 7.
    Jameson, C. J.; Mason, J. In Multinuclear NMR, Mason, J., Ed; Plenum Press, New York, 1987; Chap. 3, pp. 51–88.Google Scholar
  8. 8.
    Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortíz, J.V.; Foresman, J. B.; Peng, C.Y.; Ayala, P. Y.; Chen, W.; Wong, M.W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; González, C.; Pople, J. A., Gaussian 94, Gaussian, Inc., Pittsburgh, PA, 1995.Google Scholar
  9. 9.
    Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Gaussian, Inc., Pittsburgh, PA, 1998.Google Scholar
  10. 10.
    Becke, A. D. J. Chem. Phys. 1993, 98, 5648; Lee, C.; Yang,W.; Parr, R. G. Phys. Rev. B, 1988, 37, 785.Google Scholar
  11. 11.
    Hariharan, P. A.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213; Krishnam, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1984, 80, 3265.Google Scholar
  12. 12.
    Ditchfield, R. Mol. Phys. 1974, 27, 789.Google Scholar
  13. 13.
    Boys, S. B.; Bernardi, F. Mol. Phys. 1970, 19, 553.Google Scholar
  14. 14.
    Suzuki, S.; Green, P. G.; Bumgarner, R. E.; Dasgupta, S.; Goddard, W. A.; Blake, G. A. Science 1992, 257, 942.Google Scholar
  15. 15.
    du Vernet, R.; Boekelheide, V. Proc. Natl. Acad. Sci. USA 1974, 71, 2961.Google Scholar
  16. 16.
    Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, A. H.; Hommes, N. J. R. v. E. J. Amer. Chem. Soc. 1996, 118, 6317.Google Scholar
  17. 17.
    Cybulski, S. M.; Bishop, D. M. Mol. Phys. 1998, 93, 739.Google Scholar
  18. 18.
    Alkorta, I.; Elguero, J. Struct. Chem. 1998, 9, 187.Google Scholar
  19. 19.
    Jackowski, K. J. Mol. Struct. (Theochem.) 1994, 303, 239.Google Scholar
  20. 20.
    Jackowski, K. Chem. Phys. Lett. 1992, 194, 167.Google Scholar
  21. 21.
    Jameson, C. J.; Jameson, A. K.; Oppusunggu, D.; Wille, S.; Burrell, P. M.; Mason J. J. Chem. Phys. 1981, 74, 81.Google Scholar
  22. 22.
    Witanowski, M.; Stefaniak, L.; Webb, G. A. Ann. Rep. NMR Spectroscopy, Webb, G. A., Ed., Academic Press, London, 1993; Vol. 25, p. 212.Google Scholar
  23. 23.
    Manalo, M. N.; de Dios, A. C.; Cammi, R. J. Chem. Phys. 2000, 104, 9600.Google Scholar

Copyright information

© Plenum Publishing Corporation 2001

Authors and Affiliations

  • Ibon Alkorta
    • 1
  • Isabel Rozas
    • 1
  • María Luisa Jimeno
    • 1
  • José Elguero
    • 1
  1. 1.Instituto de Química Médica (C.S.I.C.)MadridSpain

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