Keto-Enol Tautomerism. I. The Calorimetrical Determination of the Equilibrium Constant for Keto-Enol Tautomerism for Cyclopentanone

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Abstract
The enol content of cyclopentanone was determined by calorimetrical measurement of the enthalpy of hydrolysis of cyclopentenyl methyl ether to cyclopentanone with the assumption that the thermodynamics of hydrolysis of any ROMe to ROH is the same as that for any other ROMe. The enthalpy of the ketonization of cyclopentenol was determined to be −7.87 kcal/mol in the liquid phase and −11.66 kcal/mol in the gas phase, at 25 °C. The enol content of cyclopentanone in the gas phase at 25 °C was found to be 2.5×10−7%