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

Patricia Pérez, Alejandro Toro-Labbé

Research output: Contribution to journalArticlepeer-review

69 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1557-1562
Number of pages6
JournalJournal of Physical Chemistry A
Volume104
Issue number7
DOIs
Publication statusPublished - 24 Feb 2000

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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