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

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.

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Literature cited

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Additional information

For a preliminary communication, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 550–555, March, 1971.

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Bogdanov, V.S., Negrebetskii, V.V., Korenevskii, V.A. et al. Investigation of the tautomerism of 3-amino-2-acetyl-2-cyclohexene-1-ones by the NMR method. Russ Chem Bull 20, 484–488 (1971). https://doi.org/10.1007/BF00852035

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Keywords

  • Hydrogen
  • Nitrogen
  • Hydrogen Bond
  • Chemical Shift
  • Nitrogen Atom