Advertisement

Conformational analysis of benzo-15-crown-5 and 2,3-(4′-benzoyl)benzo-15-crown-5

  • O. A. Raevskii
  • V. V. Tkachev
  • V. P. Kazachenko
  • A. N. Razdol'skii
  • I. I. Bulgak
  • V. E. Zubareva
Physical Chemistry
  • 23 Downloads

Conclusions

  1. 1.

    An x-ray structure analysis has revealed substantial diferrences in the conformational states of 2,3-(4′-benzoyl)benzo-15-crown-5 and benzo-15-crown-5 in the crystal phase, differences related to realization of a trans-gauche-gauche' conformation in one COCCOC fragment in the 2,3-(4′-benzoyl)benzo-15-crown-5.

     
  2. 2.

    In nonpolar solvents, an equilibrium of several structures is realized in both compounds, an equilibrium with the participations of trans-gauche-trans, trans-gauche-gauche and trans-gauche-gauche' conformations. In a polar medium, there are no indications of the trans-gauch-gauche' conformation.

     
  3. 3.

    Upon complexation of the ligands with calcium thiocyanate in acetonitrile, there are spectral indications of complexes with differing stoichiometry, with a large contribution of the structure from trans-gauche-trans conformations.

     

Keywords

Calcium Acetonitrile Structure Analysis Thiocyanate Benzoyl 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    M. Hiraoka, Crown Compounds: Their Characteristics and Applications, Elsevier, New York (1982).Google Scholar
  2. 2.
    N. V. Lukoyanov, O. A. Raevskii, A. S. Shtepanek, and T. N. Kudrya, Biol. Membrany,1, 379 (1984).Google Scholar
  3. 3.
    N. V. Lukoyanov, G. I. Van'kin, L. V. Zhuravleva, et al., Biol. Membrany,2, 71 (1985).Google Scholar
  4. 4.
    N. V. Lukoyanov, (Likojanov), G. I. Vankin, V. A. Panarin, and O. A. Raevskii (Raevsky), Proceedings of 11th International Symposium on Macrocyclic Chemistry, Florence (1986), p. 63.Google Scholar
  5. 5.
    M. N. Hughes, The Inorganic Chemistry of Biological Processes, Wiley-Interscience, New York (1981).Google Scholar
  6. 6.
    U. Burkert and N. L. Allinger (eds.), Molecular Mechanics, American Chemical Society, Washington, D.C. (1982).Google Scholar
  7. 7.
    V. I. Andrianov, Z. Sh. Safina, and E. L. Tarnopol'skii, Instructions for Operation with Rentgen-75 Program [in Russian], OIKhF Akad. Nauk SSSR, Chernogolovka (1975).Google Scholar
  8. 8.
    H. Dodziuk, H. von Voithenberg, and N. C. Allindger, Tetrahedron,38, 2811 (1982); H. D. Beckhaus, Chem. Ber.,116, 86 (1983).Google Scholar
  9. 9.
    I N. Hanson, Acta Crystallogr. B,34, 1026 (1978).Google Scholar
  10. 10.
    M. A. Buch and M. R. Truter, J. Chem. Soc., Perkin Trans. 2, 341 (1972).Google Scholar
  11. 11.
    P. R. Mallinson and M. R. Truter, J. Chem. Soc., Perkin Trans. 2, 1818 (1972).Google Scholar
  12. 12.
    J. Ogava, M. Ohta, M. Sakaribara, et al., Bull. Chem. Soc. Jpn.,50, 650 (1977); H. Matsuura and T. Miyazzawa, J. Chem. Soc., Perkin Trans. 2,41, 1798 (1968).Google Scholar
  13. 13.
    M. Fouassier and J. S. Lasseques, J. Chem. Phys.,75, 865 (1978).Google Scholar
  14. 14.
    O. A. Raevskii, S. V. Trepalin, V. E. Zubareva, and D. G. Batyr, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1574 (1985).Google Scholar
  15. 15.
    R. M. Izatt, J. S. Bradshaw, A. S. Nielson, et al., Chem. Rev.,85, 271 (1985).Google Scholar
  16. 16.
    J. D. Owen, J. Chem. Soc., Dalton Trans., 1418 (1978).Google Scholar

Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • O. A. Raevskii
    • 1
    • 2
    • 3
  • V. V. Tkachev
    • 1
    • 2
    • 3
  • V. P. Kazachenko
    • 1
    • 2
    • 3
  • A. N. Razdol'skii
    • 1
    • 2
    • 3
  • I. I. Bulgak
    • 1
    • 2
    • 3
  • V. E. Zubareva
    • 1
    • 2
    • 3
  1. 1.Institute of Physiologically Active SubstancesAcademy of Sciences of the USSRChernogolovka
  2. 2.N. N. Semenov Institute of Chemical PhysicsAcademy of Sciences of the USSR, Chernogolovka BranchUSSR
  3. 3.Institute of ChemistryAcademy of Sciences of the Moldavian SSRKishinev

Personalised recommendations