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Conformational analysis of benzo-15-crown-5 and 2,3-(4′-benzoyl)benzo-15-crown-5

  • Physical Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    An x-ray structure analysis has revealed substantial diferrences in the conformational states of 2,3-(4′-benzoyl)benzo-15-crown-5 and benzo-15-crown-5 in the crystal phase, differences related to realization of a trans-gauche-gauche' conformation in one COCCOC fragment in the 2,3-(4′-benzoyl)benzo-15-crown-5.

  2. 2.

    In nonpolar solvents, an equilibrium of several structures is realized in both compounds, an equilibrium with the participations of trans-gauche-trans, trans-gauche-gauche and trans-gauche-gauche' conformations. In a polar medium, there are no indications of the trans-gauch-gauche' conformation.

  3. 3.

    Upon complexation of the ligands with calcium thiocyanate in acetonitrile, there are spectral indications of complexes with differing stoichiometry, with a large contribution of the structure from trans-gauche-trans conformations.

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Authors and Affiliations

  1. Institute of Physiologically Active Substances, Academy of Sciences of the USSR, Chernogolovka

    O. A. Raevskii, V. V. Tkachev, V. P. Kazachenko, A. N. Razdol'skii, I. I. Bulgak & V. E. Zubareva

  2. N. N. Semenov Institute of Chemical Physics, Academy of Sciences of the USSR, Chernogolovka Branch, USSR

    O. A. Raevskii, V. V. Tkachev, V. P. Kazachenko, A. N. Razdol'skii, I. I. Bulgak & V. E. Zubareva

  3. Institute of Chemistry, Academy of Sciences of the Moldavian SSR, Kishinev

    O. A. Raevskii, V. V. Tkachev, V. P. Kazachenko, A. N. Razdol'skii, I. I. Bulgak & V. E. Zubareva

Authors
  1. O. A. Raevskii
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  2. V. V. Tkachev
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  3. V. P. Kazachenko
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  4. A. N. Razdol'skii
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  5. I. I. Bulgak
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  6. V. E. Zubareva
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 833–838, April, 1989.

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Raevskii, O.A., Tkachev, V.V., Kazachenko, V.P. et al. Conformational analysis of benzo-15-crown-5 and 2,3-(4′-benzoyl)benzo-15-crown-5. Russ Chem Bull 38, 748–753 (1989). https://doi.org/10.1007/BF00953285

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  • DOI: https://doi.org/10.1007/BF00953285

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