Theoretica chimica acta

, Volume 51, Issue 1, pp 65–78 | Cite as

Structure and solvation of nitrobenzene and 1,4-dinitrobenzene radical anions

  • Jens Spanget-Larsen
Original Investigations


An INDO method extended to include a contribution from the solvent by means of an effective solvent field (INDO-ESF) and based on properly optimized geometries is applied to the nitrobenzene and 1,4-dinitrobenzene radical anions. The hyperfine couplings and their solvent sensitivities are reproduced within a planar structure of the radicals. The behaviour of14N and17O splittings in derivatives with twisted nitro groups is accounted for with no difficulty.

Key words

INDO method with inclusion of an effective solvent field Nitrobenzene 1,4-dinitrobenzene radical anions, spin distribution and geometries of ∼ 


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  1. 1.
    Geske, D. H.: Progr. Phys. Org. Chem.4, 125 (1967), and Refs. thereinGoogle Scholar
  2. 2.
    Piette, L. H., Ludwig, P., Adams, R. N.: J. Am. Chem. Soc.84, 4212 (1962)CrossRefGoogle Scholar
  3. 3.
    Ludwig, P., Layloff, T., Adams, R. N.: J. Am. Chem. Soc.86, 4568 (1964)CrossRefGoogle Scholar
  4. 4.
    Geske, D. H., Ragle, J. L.: J. Am. Chem. Soc.83, 3532 (1961)CrossRefGoogle Scholar
  5. 5.
    Geske, D. H., Ragle, J. L., Bambanek, M. A., Balch, A. L.: J. Am. Chem. Soc.86, 987 (1964)CrossRefGoogle Scholar
  6. 6.
    Gendell, J., Freed, J. H., Fraenkel, G. K.: J. Chem. Phys.37, 2832 (1962)CrossRefGoogle Scholar
  7. 7.
    Rieger, P. H., Fraenkel, G. K.: J. Chem. Phys.39, 609 (1963)CrossRefGoogle Scholar
  8. 8.
    Symons, M. C. R.: Advan. Phys. Org. Chem.1, 283 (1963)CrossRefGoogle Scholar
  9. 9.
    Fox, W. M., Gross, J. M., Symons, M. C. R.: J. Chem. Soc. (A) 448 (1966); Gross, J. M., Symons, M. C. R.: J. Chem. Soc. (A) 451 (1966)Google Scholar
  10. 10.
    Gulick, W. M., Jr., Geske, D. H.: J. Am. Chem. Soc.87, 4049 (1965)CrossRefGoogle Scholar
  11. 11.
    Gulick, W. M., Jr., Geiger, W. E., Jr., Geske, D. H.: J. Am. Chem. Soc.90, 4218 (1968)CrossRefGoogle Scholar
  12. 12.
    Parrish, R. G., Hall, G. S., Gulick, W. M., Jr.: Mol. Phys.26, 1121 (1973)Google Scholar
  13. 13.
    Swartz, G. L., Gulick, W. M., Jr.: Mol. Phys.30, 869 (1975)Google Scholar
  14. 14.
    Schreiner, K., Lotz, A., Aurich, H. G., Berndt, A.: Tetrahedron31, 2117 (1975)CrossRefGoogle Scholar
  15. 15.
    Gulick, W. M., Jr., Swartz, G. L., Parrish, R. G.: J. Magn. Reson.22, 81 (1976)Google Scholar
  16. 16.
    Pople, J. A., Beveridge, D. L., Dobosh, P. A.: J. Am. Chem. Soc.90, 4201 (1968); Pople, J. A., Beveridge, D. L.: Approximate molecular orbital theory. New York: McGraw-Hill 1970CrossRefGoogle Scholar
  17. 17.
    Beveridge, D. L., in: Semiempirical methods of electronic structure calculations, Part B, Chapt. 5, Segal, G. A., ed. New York: Plenum Press 1977Google Scholar
  18. 18.
    Gilbert, B. C., Trenwith, M.: J. Chem. Soc. Perkin II 2010 (1973)Google Scholar
  19. 19.
    Miller, C., Gulick, W. M., Jr.: Mol. Phys.27, 1185 (1974)Google Scholar
  20. 20.
    Spanget-Larsen, J.: Mol. Phys.32, 735 (1976)Google Scholar
  21. 21.
    Bingham, R. C., Dewar, M. J. S., Lo, D. H.: J. Am. Chem. Soc.97, 1302 (1975), and subsequent papersCrossRefGoogle Scholar
  22. 22.
    Bischof, P.: J. Am. Chem. Soc.98, 6844 (1976)CrossRefGoogle Scholar
  23. 23.
    McGreery, J. H., Christoffersen, R. E., Hall, G. G.: J. Am. Chem. Soc.98, 7191, 7196 (1976)CrossRefGoogle Scholar
  24. 24.
    Birnstock, F., Hofmann, H.-J., Köhler, H.-J.: Theoret. Chim. Acta (Berl.)42, 322 (1976)CrossRefGoogle Scholar
  25. 25.
    Claverie, P., Daudey, J. P., Langlet, J., Pullman, B., Piazzola, D., Huron, M. J.: J. Phys. Chem.82, 405 (1978)CrossRefGoogle Scholar
  26. 26.
    Constanciel, R., Tapia, O.: Theoret. Chim. Acta (Berl.)48, 75 (1978)CrossRefGoogle Scholar
  27. 27.
    Dolgushin, M. D., Pinchuk, V. M.: Theoret. Chim. Acta (Berl.)45, 157 (1977)CrossRefGoogle Scholar
  28. 28.
    Spanget-Larsen, J.: Theoret. Chim. Acta (Berl.)47, 315 (1978)CrossRefGoogle Scholar
  29. 29.
    Spanget-Larsen, J.: Chem. Phys. Letters44, 543 (1976)CrossRefGoogle Scholar
  30. 30.
    Quantum Chemistry Program Exchange, Indiana University: QCPE 141Google Scholar
  31. 31.
    Trotter, J.: Acta Cryst.12, 884 (1959)CrossRefGoogle Scholar
  32. 32.
    Høg, J., Nygaard, L., Sørensen, G. O.: J. Mol. Struct.1, 111 (1970)Google Scholar
  33. 33.
    Carreira, L. A., Towns, T. G.: J. Mol. Struct.41, 1 (1977)CrossRefGoogle Scholar
  34. 34.
    Mason, R. P., Harriman, J. E.: J. Chem. Phys.65, 2274 (1976)CrossRefGoogle Scholar
  35. 35.
    Braude, E. A., Sondheimer, F.: J. Chem. Soc. 3754 (1955)Google Scholar
  36. 36.
    Wepster, B. M., in: Progress in stereochemistry, Vol. 2, Chapt. 4, Klyne, W., de la Mare, P. B. D., eds. London: Butterworths 1958Google Scholar

Copyright information

© Springer-Verlag 1979

Authors and Affiliations

  • Jens Spanget-Larsen
    • 1
  1. 1.Institut für Organische Chemie der Technischen Hochschule DarmstadtDarmstadtGermany

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