Russian Chemical Bulletin

, Volume 43, Issue 1, pp 50–56 | Cite as

Spectroscopic detection of theendo-enol form of 2-acetylcyclopentane-1,3-dione

  • V. G. Avakyan
  • V. V. Gromak
  • A. Ye. Yatsenko
Physical Chemistry


According to vibrational spectroscopic data, in the gas phase at 280 °C and in crystals prepared by sublimation, 2-acetylcyclopentane-1,3-dione was established to exist not as trione 1 but as the enol-form 2 with an exo-cyclic C=C bond (v(C=C) = 1593 cm−1) and an intramolecular hydrogen bond. The enol 3 prepared by crystallization from CCl4 is also stabilized by an intramolecular H-bond but has anendo-cyclic C=C bond (v(C=C) = 1545 cm−1). In a trichloroethylene solution, both theexo- andendo-enol forms co-exist, and the percentage of the latter is ∼11 %. The frequencies in the vibrational spectra have been assigned using the normal coordinate calculation of2, 3, and their OD-analogs. The mechanism of tautomer transfer is discussed in terms of PMO theory.

Key words

tautomerism of β,β'-tricarbonyl compounds exo- andendo-enol forms of 2-acetylcyclopentane-1,3-dione 


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Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • V. G. Avakyan
    • 1
  • V. V. Gromak
    • 2
  • A. Ye. Yatsenko
    • 1
  1. 1.Institute of Petrochemical SynthesisRussian Academy of SciencesMoscowRussian Federation
  2. 2.Institute of Bioorganic ChemistryByelorussian Academy of SciencesMinskBelaruss

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