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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
  • 26 Downloads

Abstract

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.

Keywords

Oxygen Hydrogen Nitrogen Sulfur Hydrogen Bonding 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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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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