Three-membered rings

Communication 3. Taft constants of three-membered rings
  • O. A. Yuzhakova
  • V. F. Bystrov
  • R. G. Kostyanovskii
Physical Chemistry


  1. 1.

    The values of the orders of the phenyl-nitrogen bonds were calculated by the molecular orbital linear combination of atomic orbital method for groups with different states of the nitrogen atom. A linear dependence ofρn-c onσc was found, and from it the value of the bond order for the ethylenimine group was obtained by interpolation:σ 1.279.

  2. 2.

    p- and m-Fluoro-substituted phenylcyclopropanes, phenyl epoxides, styrenes, phenylacetylenes, cumenes, and m-cyclopropylbenzoic acid were synthesized.

  3. 3.

    The Taft constants for the cyclopropyl, isopropyl, vinyl, ethynyl, and epoxide groups were determined according to the chemical shifts of F19 in the NMR spectra. The constants of the cyclopropyl group were also obtained from pK of p- and m-cyclopropylbenzoic acids.



Phenyl Vinyl Styrene Nitrogen Atom Epoxide 
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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    V. F. Bystrov, R. G. Kostyanovskii, O. A. Pan'shin, A. U. Scepanyants, and O. A. Yuzhakova, Optika i Spektroskopiya,19, No. 2, 217 (1965); R. G. Kostyanovskii, O. A. Yuzhakova, and V. F. Bystrov, Zh. Vses. khim. obshch. im. D. I. Mendeleeva, No. 2, 229 (1965).Google Scholar
  2. 2.
    V. F. Bystrov, O. A. Yuzhakova, and R. G. Kostyanovskii, DAN SSSR,147, 843 (1962).Google Scholar
  3. 3.
    R. W. Taft, E. Price, I. R. Fox, I. C. Lewis, K. K. Andersen, and G. T. Davis, J. Amer. Chem. Soc.,85, 709, 3146 (1963).Google Scholar
  4. 4.
    R. W. Taft and I. C. Lenic, J. Amer. Chem. Soc.,80, 2436 (1958); R. W. Taft, S. Ehrenson, I. C. Lewis, and R. E. Glick, J. Amer. Chem. Soc.,81, 5352 (1959).Google Scholar
  5. 5.
    R. Daudel, R. Lefebvre, and C. Moser, Quantum Chemistry, Methods and Applications, Inters. Publ. New York (1959).Google Scholar
  6. 6.
    G. S. Kolesnikov, Syntheses of Vinyl Derivatives of Aromatic and Heterocyclic Compounds [in Russian], Izd. AN SSSR, Moscow (1960).Google Scholar
  7. 7.
    C. D. Cook and S. S. Danyluk, Tetrahedron,19, N1, 177 (1963).Google Scholar
  8. 8.
    R. Ya. Levina, P. A. Gembitskii, L. P. Guseva, and P. K. Agasyan, Zh. obshch. khimii,34, 146 (1964); Yu. S. Shabarov, V. K. Potapov, and R. Ya. Levina, Zh. obshch. khimii,34, 2832 (1964).Google Scholar
  9. 9.
    G. Vavon and P. Mottez, Compt. rend.,218, 558 (1944).Google Scholar
  10. 10.
    D. E. Pearson, J. Organ. Chem.,23, 1412 (1958).Google Scholar
  11. 11.
    G. Wittig and K. Schwarzenbach, Liebigs Ann. Chem.,650, 1 (1961).Google Scholar
  12. 12.
    H. H. Jaffe, Chem. Rev.,53, 191 (1953).Google Scholar
  13. 13.
    V. A. Pal'm, Uspekhi khimii,30, 1069 (1961).Google Scholar

Copyright information

© Consultants Bureau 1966

Authors and Affiliations

  • O. A. Yuzhakova
    • 1
  • V. F. Bystrov
    • 1
  • R. G. Kostyanovskii
    • 1
  1. 1.Institute of Chemical PhysicsAcademy of Sciences of the USSRUSSR

Personalised recommendations