Advertisement

Conformations of the methyl and aryl esters of the arylsulfonic acids

  • G. G. Butenko
  • A. N. Vereshchagin
  • A. B. Remizov
  • R. H. Nurullina
Physical Chemistry
  • 20 Downloads

Conclusions

  1. 1.

    The substituted methylarylsulfonates and arylarylsulfonates exist as mixtures of trans and gauche conformers, the latter predominating at equilibrium (∼70%).

     
  2. 2.

    The angle of aryl group rotation relative to the Csp3-S-O plane is 43° in the methylphenylsulfonates and the methyl-p-tolylsulfonates and 75° in the methyl-p-bromophenylsulfonates.

     
  3. 3.

    As a result of electron-acceptor effects from the SO2 group, the S-O-C plane of the arylsulfonic acids esters are almost perpendicular to the aromatic ring.

     

Keywords

Methyl Ester Aromatic Ring Acid Ester Group Rotation 
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.
    B. A. Arbuzov, S. G. Vul'fson, O. A. Samarina, and A. N. Vereshchagin, Izv. Akad. Nauk SSSR, Ser. Khim., 94 (1976).Google Scholar
  2. 2.
    B. A. Arbuzov, A. B. Remizov, G. G. Butenko, and A. N. Vereshchagin, Izv. Akad. Nauk SSSR, Ser. Khim., 2006 (1978).Google Scholar
  3. 3.
    A. B. Remizov, A. I. Fishman, and G. G. Butenko, Zh. Obshch. Khim.,47, 1204 (1977).Google Scholar
  4. 4.
    I. Hargittai, G. Schultz, and M. Kolonits, J. Chem. Soc. Dalton Trans., 1299 (1977).Google Scholar
  5. 5.
    O. Exner, Z. Fidlerova, and V. Jehlicka, Collect. Czech. Chem. Commun.,33, 2019 (1968).Google Scholar
  6. 6.
    Yu. A. Pentin, Contemporary Problems in Physical Chemistry [in Russian], Vol. 1, Izv. Mosk. Univ. (1968), p. 5.Google Scholar
  7. 7.
    G. N. Zhizhin and Kh. E. Sterin, Zh. Prikl. Spektrosk.,5, 506 (1966).Google Scholar
  8. 8.
    A. B. Remizov, Opt. Spektrosk.,39, 204 (1975).Google Scholar
  9. 9.
    A. B. Remizov and T. G. Mannifov, Zh. Prikl. Spektrosk.,25, 467 (1976).Google Scholar
  10. 10.
    J. Brunvoll and I. Hargittai, J. Mol. Struct.,30, 361 (1976).Google Scholar
  11. 11.
    A. N. Vereshchagin, I. V. Bautina, G. A. Chmutova, and S. G. Vul'fson, Izv. Akad. Nauk SSSR, Ser. Khim., 2693 (1976).Google Scholar
  12. 12.
    B. A. Arbuzov, A. P. Timosheva, S. G. Vul'fson, and A. N. Vereshchagin, Izv. Akad. Nauk SSSR, Ser. Khim., 1336 (1977).Google Scholar
  13. 13.
    B. A. Arbuzov, S. G. Vul'fson, G. G. Butenko, O. A. Samarina, A. B. Teitel'baum, and A. N. Vereshchagin, Izv. Akad. Nauk SSSR, Ser. Khim., 86 (1976).Google Scholar
  14. 14.
    N. J. White, J. Chem. Soc., 1280 (1972).Google Scholar
  15. 15.
    C. Altona, Acta Crystallogr.,A25, 141 (1969).Google Scholar
  16. 16.
    P. L. Johnson, Tetrahedron,28, 2893 (1972).Google Scholar
  17. 17.
    R. P. Arshinova, S. G. Vul'fson, S. D. Ibragimova, E. T. Kukmenev, and B. A. Arbuzov, Izv. Akad. Nauk SSSR, Ser. Khim., 1241 (1976).Google Scholar
  18. 18.
    B. A. Arbuzov, R. P. Arshinova, T. D. Sorokina, A. B. Remizov, and G. E. Koroleva, Izv. Akad. Nauk SSSR, Ser. Khim., 2006 (1977).Google Scholar
  19. 19.
    C. Glidewell, D. W. H. Rankin, A. G. Roliette, G. M. Sheldrich, and J. M. Freeman, Trans. Faraday Soc.,65, 2621 (1969).Google Scholar
  20. 20.
    V. I. Fedoseeva, Yu. Pentin, T. L. Krasnova, and E. A. Chernyshev, Zh. Prikl. Spektrosk.,24, 69 (1976).Google Scholar
  21. 21.
    K. Weygand and G. Hilgetag, Experimental Methods in Organic Chemistry [Russian translation], Khimiya (1968), p. 620.Google Scholar

Copyright information

© Plenum Publishing Corporation 1980

Authors and Affiliations

  • G. G. Butenko
    • 1
    • 2
  • A. N. Vereshchagin
    • 1
    • 2
  • A. B. Remizov
    • 1
    • 2
  • R. H. Nurullina
    • 1
    • 2
  1. 1.V. I. Ul'yanov-Lenin Kazan State UniversityUSSR
  2. 2.A. E. Arbuzov Institute of Organic and Physical ChemistryKazan Branch of the Academy of Sciences of the USSRUSSR

Personalised recommendations