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Applied Spectroscopy

Applied Spectroscopy


  • Vol. 50, Iss. 11 — Nov. 1, 1996
  • pp: 1408–1412

Keto-Enol Tautomerism of Dimedone Studied by Dynamic NMR

Antonio Martínez-Richa, Guillermo Mendoza-Díaz, and Pedro Joseph-Nathan

Applied Spectroscopy, Vol. 50, Issue 11, pp. 1408-1412 (1996)

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The keto-enol tautomeric equilibrium of dimedone has been investigated by high-resolution 13C NMR spectroscopy. Kinetic information of the solution keto-enol tautomerism for dimedone in DMSO, in the temperature range of 25-85 °C, was derived from line shape measurements in a 75-MHz spectrometer. A value of 3.43 Kcal/mol was found for the Arrhenius activation energy Ea and of 1.07 x 106 s-1 for the pre-exponential factor A. With the use of the observed chemical shifts in the high-resolution 13C-NMR spectra of dimedone in the solid state, an estimate coalescence temperature of 240 K for dimedone in DMSO was obtained by extrapolation of the experimental curve. The estimated free energy of activation at the coalescence temperature, ΔGc, is 10.8 Kcal/mol. Finally, the 13C spin-lattice relaxation times, T1(13C), in solid dimedone were measured as a function of temperature in the range of 25 to 90 °C. The data are discussed in terms of the different motional environments that result from the geometric restrictions imposed by hydrogen bonding in the crystal structure.

Antonio Martínez-Richa, Guillermo Mendoza-Díaz, and Pedro Joseph-Nathan, "Keto-Enol Tautomerism of Dimedone Studied by Dynamic NMR," Appl. Spectrosc. 50, 1408-1412 (1996)

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