NMR study of coupling effects

5.13C NMR spectra, electron structures, and rotational isomerism of certain chlorosubstituted alkoxy- and alkylthioethenes
  • V. M. Bzhezovskii
  • B. A. Trofimov
  • G. A. Kalabin
  • V. V. Keiko
  • D. F. Kushnarev
  • A. N. Mirskova
  • E. F. Zorina
  • A. S. Atavin
Physical Chemistry
  • 20 Downloads

Conclusions

  1. 1.

    Study has been made of the13C NMR spectra of certain 1-alkoxy-2-chloroethenes and 1-alitoxy- and 1-alkylthio-2,2-dichloroethenes. On the basis of an analysis of the magnitude and character of the chemical shifts of the carbon atoms of the vinyl fragment, and the results of calculations on the potential energy for internal rotation, it was concluded that an increase in the size of the alkyl substituent eventually leads to breakdown of the p-π coplanarity in the 1-alkoxy-2-chloroethenes. The cis isomers of these compounds, and the 1-alkoxy-2,2-dichloroethenes, exist in gauche conformations. The s-trans conformation is most probable for the 1-alkylthio-2,2-dichloroethenes, regardless of the size of the alkyl substituent.

     
  2. 2.

    The difference in chemical shifts of the double-bond carbons parallels the known relative activities of the gem-dichlorovinyl ethers and sulfides, and their unsaturated analogs, in reactions with electrophilic compounds.

     

Keywords

Sulfide Carbon Atom Chemical Shift Potential Energy Vinyl 

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Copyright information

© Plenum Publishing CorporationPlenum Publishing Corporation 1977

Authors and Affiliations

  • V. M. Bzhezovskii
    • 1
    • 2
  • B. A. Trofimov
    • 1
    • 2
  • G. A. Kalabin
    • 1
    • 2
  • V. V. Keiko
    • 1
    • 2
  • D. F. Kushnarev
    • 1
    • 2
  • A. N. Mirskova
    • 1
    • 2
  • E. F. Zorina
    • 1
    • 2
  • A. S. Atavin
    • 1
    • 2
  1. 1.Irkutsk Institute of Organic ChemistrySiberian Branch of the Academy of Sciences of the USSRUSSR
  2. 2.A. A. Zhdanov Irkutsk State UniversityUSSR

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