Manifestation of enol鈥揺nol tautomerism in IR spectra of 2-acetylcyclopentanone-d₁

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• 作者：V. P. Glazunov (1) glazunov@piboc.dvo.ru
  D. V. Berdyshev (1)
  V. A. Denisenko (1)
• 关键词：IR spectrum &#8211 ; 2 ; acetylcyclopentanone &#8211 ; enol&#8211 ; enol tautomerism
• 刊名：Journal of Applied Spectroscopy
• 出版时间：September 2011
• 出版年：2011
• 期刊代码：14_00219037
• 类别：law
• 卷：78
• 期：4
• 页码：489-500
• 数据来源：sp

摘要

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.