Spectroscopic effects and intramolecular interactions in the1H and13C NMR spectra of five-membered N-vinyllactams

  • A. V. Afonin
  • B. V. Trzhtsinskaya
  • N. D. Abramova
  • E. V. Apakina
  • A. V. Vashchenko
Physical Chemistry


In 1-vinylpyrrolidone, 1-vinyl-1,2,4-triazole-5-ones, 1,3-divinylimidazolidine-2-thione, and 1-vinylbenzimidazole-1-thione the vinyl groups exist predominantly in the s-trans-, but in 1-vinyl-4,5-diphenylimidazole-2-ones in the s-cis(0)-conformations relative to the exocyclic heteroatom. In 1-vinylbenzimidazole-2-ones, 3-vinylbenzoxazole-2-one, and 1-vinylindole-2,3-diones the vinyl group is present as a mixture of the s-cis(0)- and s-trans(0)-conformations. According to1H and13C NMR results there are specific intramolecular interactions in 1-vinylpyrrolidone and in 1,3-divinylimidazolidine-2-thione resembling weak hydrogen bonding between the α-hydrogen atoms of the vinyl group and the oxygen or the sulfur atom. In 1-vinylsuccinimide, 2-vinylphthalimide, and 1,3-divinyl-4,5-diphenylimidazole-2-one there is the same type of interaction with the β-cis-hydrogen atom of the vinyl group, while in 1,3-divinyl-1,2,4-triazole-5-one there is interaction between the same hydrogen atom and the nitrogen atom.


Oxygen Hydrogen Nitrogen Sulfur Hydrogen Bonding 
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Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • A. V. Afonin
    • 1
  • B. V. Trzhtsinskaya
    • 1
  • N. D. Abramova
    • 1
  • E. V. Apakina
    • 1
  • A. V. Vashchenko
    • 1
  1. 1.Irkutsk Institute of Organic Chemistry, Siberian BranchAcademy of Sciences of the USSRUSSR

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