Advertisement

Theoretica chimica acta

, Volume 33, Issue 1, pp 43–50 | Cite as

The electronic structure of bicyclo [2.2.1] heptane and of bicyclo [2.2.2] octane

  • J. M. Lehn
  • G. Wipff
Commentationes

Abstract

An ab initia SCF-LCAO-MO study of bicyclo [2.2.1] heptane(I) and of bicyclo [2.2.2] octane(II) has been performed. The electronic structure and the nature of the molecular orbitals and of the bonds have been analyzed. Interactions between fragment orbitals may be recognized. The bridgehead C-H bonds interact dominantly “through-space” in I and “through-bond” in II. Some relations between electronic structure and molecular properties are discussed.

Key words

Bicyclo[2.2.1]heptane Bicyclo[2.2.2]octane 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Newton,M.D., Schulman,J.M: J. Am. Chem. Soc. 94, 773 (1972)Google Scholar
  2. 2.
    Lehn,J.M., Wipff,G.: Chem. Phys. Letters 15, 450 (1972)Google Scholar
  3. 3.
    Lehn,J.M., Wipff,G.: Theoret. Chim. Acta (Berl.) 28, 223 (1973)Google Scholar
  4. 4.
    Yonezawa,T., Shimizu,K., Morimoto,H., Kato,H.: Nippon Kagaku Zasshi 90, 142 (1969)Google Scholar
  5. 5.
    Morino,Y., Kuchitsu,K., Yokozeki,A.: Bull. Chem. Soc. Japan 40, 1552 (1967)Google Scholar
  6. 6.
    Ermer,O., Dunitz,J.D.: Helv. Chim. Acta 52, 1861 (1969)Google Scholar
  7. 7.
    Cameron,A.F., Ferguson,G., Morris,D.G.: J. Chem. Soc. (B), 1968, 1249Google Scholar
  8. 8.
    Haselbach,E., Schmelzer,A.: Helv. Chim. Acta 54, 1299 (1971)Google Scholar
  9. 9.
    Salem,L., Wright,J.S.: J. Am. Chem. Soc. 91, 5947 (1969)Google Scholar
  10. 10.
    Jorgensen,W.L., Salem,L.: The organic chemist's book of orbitals. New York: Academic Press 1973Google Scholar
  11. 11.
    Hoffmann,R., Imamura,A., Hehre,W.J.: J. Am. Chem. Soc. 90, 1499 (1968)Google Scholar
  12. 12.
    Hoffmann,R.: Accounts Chem. Research 4, 1 (1971)Google Scholar
  13. 13.
    Wipff,G.: Thèse de 3° Cycle, Université Louis Pasteur, Strasbourg (1971)Google Scholar
  14. 14.
    Foster,J.M., Boys,S.F.: Rev. Mod. Phys. 32, 300 (1960)Google Scholar
  15. 15.
    Tori,K., Muneyuki,R., Tanida,H.: Can. J. Chem. 41, 3142 (1963)Google Scholar
  16. 16.
    Srinivasan,R., Sonntag,F.I.: J. Am. Chem. Soc. 89, 407 (1967)Google Scholar
  17. 17.
    Kooyman,E.C., Vegter,G.C.: Tetrahedron 4, 382 (1958)Google Scholar
  18. 18.
    Wiberg,K.B., Williams,V.Z., Jr.: J. Org. Chem. 35, 369 (1970)Google Scholar
  19. 19.
    Bickel,A.F., Knotnerus,J., Kooyman,E.C., Vegter,G.C.: Tetrahedron 9, 230 (1960)Google Scholar
  20. 20.
    Bischof,P., Hashmall,J.A., Heilbronner,E., Hornung,V.: Helv. Chim. Acta 52, 1745 (1969)Google Scholar
  21. 21.
    Hoffmann,R., Mollère,P.D., Heilbronner,E.: J. Am. Chem. Soc. 95, 4860 (1973)Google Scholar

Copyright information

© Springer-Verlag 1974

Authors and Affiliations

  • J. M. Lehn
    • 1
  • G. Wipff
    • 1
  1. 1.Institut de ChimieUniversité Louis PasteurFrance

Personalised recommendations