Characterization of Keto-Enol Tautomerism of Acetyl Derivatives from the Analysis of Energy, Chemical Potential, and Hardness

Patricia Pérez, Alejandro Toro-Labbé

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

68 Citas (Scopus)

Resumen

We present a theoretical study of the substituent effects on keto ⇌ enol equilibria in 10 acetyl derivatives (CH3COX, X = H, OH, CH3,OCH3, NH2, N(CH3)2, OCHO, F, Cl and Br). The analysis performed in terms of the potential energy, electronic chemical potential, and molecular hardness leads to the following results: (a) in the whole series, the keto isomers are more stable than the enol ones; (b) it is shown that the HSAB principle may explain the relative stability of the keto and the enol species; (c) accurate activation barriers are predicted from a modified Marcus-like equation that contains the force constants associated to reactants and products and to the imaginary frequency of the transition states; (d) the energy and hardness profiles are opposite to each other, verifying the principle of the maximum hardness.

Idioma originalInglés
Páginas (desde-hasta)1557-1562
Número de páginas6
PublicaciónJournal of Physical Chemistry A
Volumen104
N.º7
EstadoPublicada - 24 feb 2000

Áreas temáticas de ASJC Scopus

  • Química física y teórica

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