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Crystallography Reports

, Volume 51, Issue 3, pp 434–447 | Cite as

Crystal and molecular structure of a series of 15-crown-5-containing styryl heterocycles and their dimethoxy substituted analogues

  • L. G. Kuz’mina
  • O. A. Fedorova
  • E. N. Andryukhina
  • M. M. Mashura
  • S. P. Gromov
  • M. V. Alfimov
Structure of Organic Compounds
  • 28 Downloads

Abstract

A comparative study of the molecular geometry and crystal packing of crown-containing styryl heterocycles and their dimethoxy substituted analogues is performed. It is established that all the compounds exhibit an identical type of distortions of the geometry of the central styryl fragment. These are the localization of the π-electron density at the ethylene bond and the bond alternation in a half of the phenyl ring due to the conjugation of lone electron pairs of the oxygen substituents with the chromophore system of the molecule. A comparative analysis of the crystal packings of the compounds reveals extended separate hydrophilic and hydrophobic regions. The hydrophilic regions are built of crown ether fragments, and the hydrophobic regions consist of π-conjugated and aromatic molecular fragments. The hydrophobic regions are characterized by a wide variety of packing motifs, among which stacking packing is absent. For two compounds, the formation of sandwich dimers that are preorganized to enter into the photochemical [2 + 2]cycloaddition reaction is observed.

PACS numbers

61.64.Hq 

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Copyright information

© Pleiades Publishing, Inc. 2006

Authors and Affiliations

  • L. G. Kuz’mina
    • 1
  • O. A. Fedorova
    • 2
  • E. N. Andryukhina
    • 2
  • M. M. Mashura
    • 2
  • S. P. Gromov
    • 2
  • M. V. Alfimov
    • 2
  1. 1.Kurnakov Institute of General and Inorganic ChemistryRussian Academy of SciencesMoscowRussia
  2. 2.Photochemistry CenterRussian Academy of SciencesMoscowRussia

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