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Basicity and structure of α,β-unsaturated ketones of the heterocyclic series

IV. Selenophene analogs of chalcone

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The protolytic equilibrium constants of 1-(2′-selenienyl)-3-phenyl-1-propenone, 1-(2′-selenienyl)-3-phenyl-3-propenone, and 1, 3-di (2′-selenienyl) propenone have been measured spectrophotometrically in solutions of sulfuric acid (monohydrate) in glacial acetic acid. The results obtained are compared with data on the basicity of chalcone and its thiophene and furan analogs. It is established that, in heterocyclic analogs of chalcone, five-membered heterocycles containing oxygen, sulfur, and selenium show an electron-donating effect which decreases in the order 2-furyl > 2-selenienyl > 2-thienyl.

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References

  1. V. F. Lavrushin, S. V. Tsukerman, A. I. Artemenko, and V. M. Nikitchenko, ZhOKh, 31, 1275, 1961; 32, 2551, 2577, 1962.

    Google Scholar 

  2. L. Bruzzi, J. Degan, and A. Fundo, Boll. sci. fac. chim. ind., Bologna, 19, 40, 1961; C. A., 55, 23040, 1961.

    Google Scholar 

  3. D. G. Manly and E. D. Amstutz, J. Org. Chem., 22, 323, 1957.

    Google Scholar 

  4. Yu. K. Yur'ev, M. A. Gal'bershtam, and A. F. Prokof'eva, Izv. VSh (Khimiya), 7, 419, 598, 1964.

    Google Scholar 

  5. I. I. Grandberg and A. N. Kost, ZhOKh, 32, 3025, 1962.

    Google Scholar 

  6. G. Pappalardo, Gazz. chim. ital., 89, 540, 551, 1959; RZhKh, 29672, 29673, 1960.

    Google Scholar 

  7. L. Chierici and G. Pappalardo, Gazz. chim. ital., 89, 560, 1959; C. A., 54, 12108, 1960.

    Google Scholar 

  8. A. Bellotti and L. Chierici, Gazz. chim. ital., 90, 1125, 1960; C. A., 55, 21095, 1961.

    Google Scholar 

  9. H. Stobbe and R. Haertel, Ann., 370, 99, 1909.

    Google Scholar 

  10. T. G. Melent'eva, L. A. Pavlova, and E. D. Venus-Danilova, ZhOKh, 34, 2267, 1964.

    Google Scholar 

  11. S. V. Tsukerman, L. A. Kutulya, V. M. Nikitchenko, and V. F. Lavrushin, ZhOKh, 33, 3180, 3186, 1963.

    Google Scholar 

  12. S. V. Tsukerman, L. A. Kutulya, and V. F. Lavrushin, KhGS [Chemistry of Heterocyclic Compounds], 803, 1965.

  13. L. M. Litvinenko and R. S. Cheshko, ZhOKh, 30, 3682, 1960.

    Google Scholar 

  14. L. M. Litvinenko, Izv. AN SSSR, OKhN, 1737, 1962.

  15. D. H. McDaniel and H. C. Brown, J. Org. Chem., 23, 420, 1958.

    Google Scholar 

  16. G. Milazzo, Gazz. chim. ital., 83, 787, 1953; C. A., 49, 2868, 1955.

    Google Scholar 

  17. H. Gerding, G. Millazzo, and H. H. K. Rossmark, Rec. trav. chim., 72, 957, 1953; 72, 957; C. A., 48, 3793, 1954.

    Google Scholar 

  18. H. C. Longuet-Higgins, Trans. Faraday Soc., 45, 173, 1949.

    Google Scholar 

  19. A. I. Kiss, Acta phys. et chem. Szeged., 5, 45, 1959; RZhKh, 21B103, 1961.

    Google Scholar 

  20. Yu. K. Yur'ev, N. N. Magdesieva, and V. V. Titov, ZhOKh, 34, 1078, 1964.

    Google Scholar 

  21. W. E. Catlin, Iowa State Coll. J. Sci., 10, 65, 1935; C. A., 30, 935, 1936.

    Google Scholar 

  22. H. Hopff and A. Krieger, Helv. Chim. Acta., 44, 1058, 1961.

    Google Scholar 

  23. T. I. Temnikova, Course in the Theoretical Bases of Organic Chemistry, 2nd ed. [in Russian], Goshkhimizdat, Leningrad, p. 224, 1962.

    Google Scholar 

  24. N. F. Hall and W. F. Spengeman, J. Am. Soc., 62, 2487, 1940.

    Google Scholar 

  25. S. V. Tsukerman, V. D. Orlov, V. F. Lavrushin, and Yu. K. Yur'ev, ZhOrKh, 1, 650, 1965.

    Google Scholar 

  26. S. V. Tsukerman, V. D. Orlov, V. P. Izvekov, V. F. Lavrushin, and Yu. K. Yur'ev, KhGS [Chemistry of Heterocyclic Compounds], 34, 1966.

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Authors and Affiliations

  1. Gor'kii Khar'kov State University, USSR

    S. V. Tsukerman, L. A. Kutulya, V. F. Lavrushin & Yu. K. Yur'ev

  2. Lomonosov Moscow State University, USSR

    S. V. Tsukerman, L. A. Kutulya, V. F. Lavrushin & Yu. K. Yur'ev

Authors
  1. S. V. Tsukerman
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  2. L. A. Kutulya
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  3. V. F. Lavrushin
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  4. Yu. K. Yur'ev
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Additional information

Forpart III, see [12].

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Tsukerman, S.V., Kutulya, L.A., Lavrushin, V.F. et al. Basicity and structure of α,β-unsaturated ketones of the heterocyclic series. Chem Heterocycl Compd 2, 271–275 (1967). https://doi.org/10.1007/BF00742365

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  • DOI: https://doi.org/10.1007/BF00742365

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