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Russian Chemical Bulletin

, Volume 58, Issue 6, pp 1192–1210 | Cite as

Design of crystal packings of styrylheterocycles and [2+2] photocycloaddition reactions in their single crystals 6. Synthesis and crystal packings of neutral crown-containing and model styrylheterocycles

  • L. G. Kuz’mina
  • A. I. Vedernikov
  • N. A. Lobova
  • S. K. Sazonov
  • S. S. Basok
  • J. A. K. Howard
  • S. P. Gromov
Full Articles

Abstract

Neutral crown-containing and model styrylheterocycles of the 4-pyridine, 4-quinoline, and 9-acridine series were synthesized under acidic catalysis. The influence of the molecular geometry of these compounds, as well as of related styrylheterocycles of the 2-benzothiazole and benzobisthiazole series, on the formation of a particular crystal packing was investigated based on X-ray diffraction data. An extension of the conjugation system in the molecules can result in the sandwich-herringbone packing motif as the only one of the three packing motifs most typical of this class of compounds. This packing provides the preorganization of the structural units for the [2+2] photocycloaddition reaction. The styrylheterocycle containing the bulky 9-acridine moiety is nonplanar due to strong intramolecular steric interactions. The packing motifs formed by nonplanar molecules do not provide the preorganization of the molecules for the [2+2] photocycloaddition. The introduction of the crown ether moiety into the benzene ring of the styrylheterocycle can decrease the predictability of the packing motif as a result of the inclusion of solvent molecules capable of hydrogen bonding with the heteroatoms of the macrocycle in the crystal structure.

Key words

styrylheterocycles synthesis X-ray diffraction study crystal packing design of crystal packings 

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Copyright information

© Springer Science+Business Media, Inc.  2009

Authors and Affiliations

  • L. G. Kuz’mina
    • 1
  • A. I. Vedernikov
    • 2
  • N. A. Lobova
    • 2
  • S. K. Sazonov
    • 2
  • S. S. Basok
    • 3
  • J. A. K. Howard
    • 4
  • S. P. Gromov
    • 2
  1. 1.N. S. Kurnakov Institute of General and Inorganic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.Photochemistry CenterRussian Academy of SciencesMoscowRussian Federation
  3. 3.A. V. Bogatsky Physico-Chemical InstituteNational Academy of Sciences of UkraineOdessaUkraine
  4. 4.Department of ChemistryUniversity of DurhamDurhamUK

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