Chemistry of Heterocyclic Compounds

, Volume 29, Issue 8, pp 926–931 | Cite as

Synthesis and X-ray diffraction and quantum-chemical analysis of 1-allyl-3-formylpyridinium bromide thiosemicarbazone

  • N. P. Erchak
  • V. Ya. Ryabova
  • A. A. Kemme
  • S. V. Belyakov


Successive alkylation of 3-pyridinecarboxaldehyde with allyl bromide and reaction of 1-allyl-3-formylpyridinium bromide with thiosemicarbazide gave 1-allyl-3-formylpyridinium bromide semicarbazone. X-ray diffraction analysis and quantum-chemical calculations with optimization of geometry were conducted on the semicarbazone synthesized. It was shown that quaternization of the nitrogen atom did not have any effect on the planarity of the heterocycle and the cationic charge was mainly localized on the thiosemicarbazone group, in which intramolecular hydrogen bonding is absent, despite the small interatomic separation of N...H-N.


Hydrogen Bonding Bromide Nitrogen Atom Alkylation Diffraction Analysis 
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Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • N. P. Erchak
    • 1
  • V. Ya. Ryabova
    • 1
  • A. A. Kemme
    • 1
  • S. V. Belyakov
    • 1
  1. 1.Latvian Institute of Organic SynthesisRiga

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