IR spectroscopy was used to show that 2-acetylcyclopentanone (2-ACPN) exists in solutions of aprotic organic solvents as a mixture of three tautomeric forms. Assignments of absorption bands in IR spectra of 2-ACPN and its deuterated analog 2-ACPN-d1 were made based on calculations of normal mode frequencies by a B3LYP/6-311++(2 d,2p) method for the gas phase and taking into account the influence of aprotic solvents in the framework of a polarizable continuum model (PCM). The enol–enol tautomeric equilibrium constant was evaluated for 2-ACPN-d1 in solutions of the aprotic solvents. The content of the diketo form of 2-ACPN was shown to depend strongly on the solvent polarity and increased with it.
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Translated from Zhurnal Prikladnoi Spektroskopii, Vol. 78, No. 4, pp. 522–534, July–August, 2009.
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Glazunov, V.P., Berdyshev, D.V. & Denisenko, V.A. Manifestation of enol–enol tautomerism in IR spectra of 2-acetylcyclopentanone-d1 . J Appl Spectrosc 78, 489–500 (2011). https://doi.org/10.1007/s10812-011-9489-7
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DOI: https://doi.org/10.1007/s10812-011-9489-7