title: Bond dissociation enthalpies of polyphenols: the importance of cooperative effects.
abstract: The hydrogen-oxygen bond dissociation energies of 3,5-di-tert-butylcatechol, 2,5-di-tert-pentylhydroquinone, propyl gallate, and octyl gallate, which represent model compounds of three important classes of naturally occurring antioxidants, have been measured by an EPR equilibration technique, and the factors determining their values have been clarified. The excellent antioxidant activity of the these polyphenols is largely due to the stabilization of the aroxyl radical due to the formation of an intramolecular hydrogen bond.
authors.affiliation: Dipartimento di Chimica Organica A. Mangini, Università di Bologna, Via S. Donato 15, I-40127 Bologna, Italy.
authors.forename: Marco
authors.initials: M
authors.lastname: Lucarini
authors.forename: Veronica
authors.initials: V
authors.lastname: Mugnaini
authors.forename: Gian Franco
authors.initials: GF
authors.lastname: Pedulli
mesh_terms: D004578:Electron Spin Resonance Spectroscopy; D005419:Flavonoids; D010636:Phenols / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D059808:Polyphenols; D017550:Spectroscopy, Fourier Transform Infrared; D013816:Thermodynamics
chemical_list: D005419:Flavonoids; D010636:Phenols; D011108:Polymers; D059808:Polyphenols