Energetic and Structural Properties of Two Phenolic Antioxidants: Tyrosol and Hydroxytyrosol

Título traducido de la contribución: Propiedades energéticas y estructurales de dos antioxidantes fenólicos

Juan Z. Dávalos, Ana C. Valderrama-Negrón, Julio R. Barrios, Vera L.S. Freitas, Maria D.M.C. Ribeiro Da Silva

Resultado de la investigación: Contribución a una revistaArtículo (Contribución a Revista)revisión exhaustiva

13 Citas (Scopus)


Theoretical and experimental studies on the energetic, structural and some other relevant physicochemical properties of the antioxidant tyrosol (1), hydroxytyrosol (1OH) molecules and the corresponding radicals 1rad and 1Orad are reported in this work. The experimental values of the gas-phase enthalpy of formation, ΔfHm0(g), in kJ·mol-1, of 1 (-302.4 ± 3.4) and 1OH (-486.3 ± 4.1) have been determined. Quantum chemical calculations, at DFT (M05-2X) and composite ab initio G3 and G4 levels of theory, provided results that served to (i) confirm the excellent consistency of the experimental measurements performed, (ii) establish that the stabilizing effect of H-bond of hydroxyethyl chain and aromatic ring (OH···π interaction) is smaller in radicals than in parent molecules, (iii) deduce - combining experimental data in isodesmic reactions - ΔfHm0(g) of radicals 1rad (-152.3 ± 4.4 kJ·mol-1) and 1Orad (-370.6 ± 3.8 kJ·mol-1), (iv) estimate a reliable O-H bond dissociation enthalpy, BDE of 1 (368.1 ± 5.6 kJ·mol-1) and of 1OH (333.7 ± 5.6 kJ·mol-1), and (v) corroborate - using "BDE criteria" - than 1OH is a more effective antioxidant than 1.

Título traducido de la contribución Propiedades energéticas y estructurales de dos antioxidantes fenólicos
Idioma originalInglés
Páginas (desde-hasta)4130-4137
Número de páginas8
PublicaciónJournal of Physical Chemistry A
EstadoPublicada - 26 abr. 2018


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