Investigation of the tautomerism of 3-amino-2-acetyl-2-cyclohexene-1-ones by the NMR method

  • V. S. Bogdanov
  • V. V. Negrebetskii
  • V. A. Korenevskii
  • A. M. Moiseenkov
  • F. A. Lakhvich
  • A. A. Akhrem
Physical Chemistry
  • 17 Downloads

Conclusions

  1. 1.

    According to the data of the NMR spectra, primary and secondary 3-amino-2-acetyl-2-cyclohexene-1-ones exist primarily in a tautomeric form, including a strong intramolecular hydrogen bond.

     
  2. 2.

    The chemical shifts of the proton of NH in the chelated ring depend substantially on the nature of the substituent at the nitrogen atom and depend little on the nature of the solvent.

     
  3. 3.

    In primary enaminodiketones, the chemical shifts of the two NH protons differ by ∼3.5 ppm, while the spin-spin interaction constants\(J_{N^{15} ,H} \) differ by 3–5 Hz, and possess the same sign.

     

Keywords

Hydrogen Nitrogen Hydrogen Bond Chemical Shift Nitrogen Atom 

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Literature cited

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Copyright information

© Consultants Bureau 1971

Authors and Affiliations

  • V. S. Bogdanov
    • 1
  • V. V. Negrebetskii
    • 1
  • V. A. Korenevskii
    • 1
  • A. M. Moiseenkov
    • 1
  • F. A. Lakhvich
    • 1
  • A. A. Akhrem
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRUSSR

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