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Russian Chemical Bulletin

, Volume 55, Issue 3, pp 559–568 | Cite as

Synthesis and structures of pyrimidinophanes containing a nitrogen atom in the bridge

  • V. E. Semenov
  • A. E. Nikolaev
  • L. F. Galiullina
  • O. A. Lodochnikova
  • I. A. Litvinov
  • A. P. Timosheva
  • V. E. Kataev
  • Yu. Ya. Efremov
  • D. R. Sharafutdinova
  • A. V. Chernova
  • Sh. K. Latypov
  • V. S. Reznik
Article

Abstract

The reactions of 1,3-bis(5-bromopentyl)-5-methyl-or 1,3-bis(5-bromopentyl)-6-methyl-uracil with benzylamine afforded pyrimidinophanes containing the nitrogen atom in the polymethylene bridge. Single-crystal X-ray diffraction study and NMR and UV spectroscopic study in solution demonstrated that the phenyl and uracil fragments in the macrocycles are in spatial proximity. Unlike the known macrocycles containing the pyrimidine ring, the pyrimidinophanes under study are conformationally rigid.

Key words

macrocyclic compounds pyrimidinophanes conformation X-ray diffraction study NMR spectroscopy hypochromic effect dipole moment 

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Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • V. E. Semenov
    • 1
  • A. E. Nikolaev
    • 1
  • L. F. Galiullina
    • 1
  • O. A. Lodochnikova
    • 1
  • I. A. Litvinov
    • 1
  • A. P. Timosheva
    • 1
  • V. E. Kataev
    • 1
  • Yu. Ya. Efremov
    • 1
  • D. R. Sharafutdinova
    • 1
  • A. V. Chernova
    • 1
  • Sh. K. Latypov
    • 1
  • V. S. Reznik
    • 1
  1. 1.A. E. Arbuzov Institute of Organic and Physical ChemistryKazan Research Center of the Russian Academy of SciencesKazanRussian Federation

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