Comparative estimate of p-π interaction in vinyl ethers and sulfides

  • B. A. Trofimov
  • É. I. Kositsyna
  • N. I. Shergina
  • S. G. Shevchenko
  • E. P. Vyalykh
Brief Communications

Conclusions

  1. 1.

    Vinyl sulfides, when they form a hydrogen bond with phenol, shift the stretching vibrations of the O-H of phenol more strongly than do the vinyl ethers; the reverse relation is observed for the saturated analogs.

     
  2. 2.

    A comparison with the data of H-bonding involving the vinyl ethers makes it possible to attribute the observed “inversion” in the basicity as being mainly due to the p-π conjugation in the vinyloxy group.

     

Keywords

Hydrogen Ether Sulfide Phenol Hydrogen Bond 

Literature cited

  1. 1.
    R.T. Hobgood, Jr., G.S. Reddy, and J.H. Goldstein, J. Phys. Chem.,67, 110 (1963).Google Scholar
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    M.C. Caserio, R.E. Pratt, and R.J. Holland, J. Am. Chem. Soc.,88, 5747 (1966).Google Scholar
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    B.A. Trofimov, N.I. Shergina, E.I. Kositsyna, A.S. Atavin, A.V. Gusarov, G.M. Gavrilova, and I.S. Emel'yanov, Reactivity of Organic Compounds [in Russian], Vol. 6, No. 22, Izd. Tartusk. Univ. (1969), p. 902.Google Scholar
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    I.M. Ginzburg, Optika i Spektroskopiya,17, 57 (1964).Google Scholar
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    L.J. Bellamy, G. Eglinton, J.F. Morman, J. Chem. Soc., 4762 (1961).Google Scholar

Copyright information

© Consultants Bureau 1972

Authors and Affiliations

  • B. A. Trofimov
    • 1
  • É. I. Kositsyna
    • 1
  • N. I. Shergina
    • 1
  • S. G. Shevchenko
    • 1
  • E. P. Vyalykh
    • 1
  1. 1.Irkutsk Institute of Organic ChemistrySiberian Branch of the Academy of Sciences of the USSRUSSR

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