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Structure and basicity of ω-substituted ethynyl 2-thienyl ketones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

By a comparison of the calculated and experimental dipole moments of ethynyl 2-thienyl ketones, it was shown that the S,O-cis conformation is the most probable one. The basicities of these compounds were estimated by means of IR spectroscopy from the shift of the band of the phenolic OH stretching vibration. The correlation relationships between the dipole moments of the ketones, their basicities, and the association constants of propiolic acids that have identical substituents attached to the triple bond were established. It is noted that the experimental characteristics found do not correlate with the different sorts ofσ substituent constants; this provides evidence for a difference in the mechanism of the interaction of the atomic groups in a number of acetylenic and aromatic molecules.

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Literature cited

  1. H. Iumbroso and P. Pastour, Comptes Rend.,261, 1279 (1965).

    Google Scholar 

  2. V. I. Minkin, Yu. A. Zhdanov, and E. N. Malysheva, Teor. i Éksperim. Khim.,7, 180 (1972).

    Google Scholar 

  3. V. I. Savin, S. A. Flegontov, and Yu. P. Kitaev, Khim. Geterotsikl. Soedin., 1188 (1970).

  4. R. I. Kruglikova and G. R. Kalinina, Zh. Organ. Khim.,7, 857 (1971).

    Google Scholar 

  5. B. I. Rogozev, V. S. Zavgorodnii, L. M. Krizhanskii, and A. A. Petrov, Zh. Obshch. Khim.,38, 2064 (1968).

    Google Scholar 

  6. Yu. A. Zhdanov and V. I. Minkin, Correlation Analysis in Organic Chemistry [in Russian], Izd. Rostovsk. Univ. (1966).

  7. V. S. Zavgorodnii, B. I. Rogozev, É. S. Sivenkov, and A. A. Petrov, Zh. Obshch. Khim.,41, 2237 (1971).

    Google Scholar 

  8. V. S. Zavgorodnii, B. I. Rogozev, É. S. Sivenkov, K. S. Mingaleva, and A. A. Petrov, Zh. Obshch., Khim.,41, 2241 (1971).

    Google Scholar 

  9. M. Charton, J. Org. Chem.,26, 735 (1961).

    Google Scholar 

  10. A. V. Iogansen, Opt. i Spektrosk.,16, 813 (1964).

    Google Scholar 

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Authors and Affiliations

  1. Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, USSR

    N. I. Golovanova, T. V. Kashik, N. I. Shergina, T. N. Bazhenova, V. I. Knutov, A. S. Nakhmanovich & Yu. L. Frolov

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  1. N. I. Golovanova
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  2. T. V. Kashik
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  3. N. I. Shergina
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  4. T. N. Bazhenova
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  5. V. I. Knutov
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  6. A. S. Nakhmanovich
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  7. Yu. L. Frolov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1481–1484, November, 1974.

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Golovanova, N.I., Kashik, T.V., Shergina, N.I. et al. Structure and basicity of ω-substituted ethynyl 2-thienyl ketones. Chem Heterocycl Compd 10, 1301–1304 (1974). https://doi.org/10.1007/BF01175083

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  • DOI: https://doi.org/10.1007/BF01175083

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