Analysis of conformations of aliphatic alcohols and ethers

  • T. M. Ivanova
  • S. F. Arkhipova
  • G. P. Kugatova-Shemyakina
Organic and Biological Chemistry


  1. 1.

    Taking into account the nonvalence interactions of the atoms, the torsion energy, and the reactions of the functional groups, we calculated the geometric conformations and the energies of the optimum conformations of the compounds CH2=CH(CH2)nR, where R = OH or OCH3, and n = 2–5.

  2. 2.

    In alcohols the most favorable conditions for the formation of an intramolecular hydrogen bond are realized when n = 2. In ethers the interaction of the unshared pairs of oxygen with the double bond can be realized in the coiled forms of molecules with n = 3, which is in agreement with their high reactivity.

  3. 3.

    The effect of replacing the hydrogen atoms by methyl groups on the potential energy of the molecules was discussed.



Oxygen Hydrogen Alcohol Methyl Ether 
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Literature cited

  1. 1.
    P. E. Petersen, C. Casey, E. P. V. Tao, A. Agtarap, and G. Thompson, J. Am. Chem. Soc.,87, 5163 (1965).Google Scholar
  2. 2.
    V. D. Dashevskii and A. I. Kitaigorodskii, Teor. i Eksperim. Khim.,3, 43 (1967).Google Scholar
  3. 3.
    E. M. Popov, V. G. Dashevskii, G. M. Lipkind, and S. F. Arkhipova, Molekul. Biol.,2, 612 (1968).Google Scholar
  4. 4.
    A. I. Kitaigorodsky and V. G. Dashewsky, Tetrahedron,24, 5917 (1968).Google Scholar
  5. 5.
    V. G. Dashevskii, Zh. Strukt. Khim.,9, 289 (1968).Google Scholar
  6. 6.
    E. M. Popov, G. M. Lipkind, S. F. Arkhipova, and V. G. Dashevskii, Molekül. Biol.,2, 622 (1968).Google Scholar
  7. 7.
    E. B. Wilson, Advan. Chem. Phys.,2, 367 (1959).Google Scholar
  8. 8.
    R. A. Scott and H. A. Scheraga, J. Chem. Phys.,42, 2209 (1966).Google Scholar
  9. 9.
    P. R. Schleyer, D. S. Trifan, and R. Baskai, J. Am. Chem. Soc.,80, 6691 (1958).Google Scholar
  10. 10.
    M. Old and H. Iwamura, Bull. Chem. Soc. Japan,32, 567 (1959).Google Scholar
  11. 11.
    J. Armand and P. Arnaud, Ann. Chim.,9, 433 (1964).Google Scholar
  12. 12.
    R. A. Scott and H. A. Scheraga, J. Chem. Phys.,44, 3054 (1966).Google Scholar
  13. 13.
    A. I. Kitaigorodskii, Organic Crystal Chemistry [in Russian], Fizmatgiz, Moscow (1955).Google Scholar
  14. 14.
    M. Oki and H. Iwamura, Bull. Chem. Soc. Japan,32, 950 (1959).Google Scholar

Copyright information

© Consultants Bureau 1974

Authors and Affiliations

  • T. M. Ivanova
    • 1
  • S. F. Arkhipova
    • 1
  • G. P. Kugatova-Shemyakina
    • 1
  1. 1.M. M. Shemyakin Institute of Natural CompoundsAcademy of Sciences of the USSRUSSR

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