35492-69-4Relevant academic research and scientific papers
Effect of Solvation on the Bond Dissociation Energies of Phenolic Antioxidants
Pedrielli, Pamela,Pedulli, Gian Franco
, p. 509 - 512 (2007/10/03)
The effect of solvent on the bond dissociation energies (BDEs) of the oxygen-hydrogen bond in substituted phenolic antioxidants has been investigated by means of an EPR technique.On changing the solvent from benzene to tert-butanol the BDE's were found to increase by ca. 2.2 kcal/mol for phenols without ortho substituents, by ca. 1 kcal/mol for 2,6-dimethyl substituted phenols while in 2,6-di-tert-butyl phenols they seem to be substantially unaffected.This behaviour has been interpreted by admitting that the BDE increase observed in tert-butanol is essentially due to the solvation of the hydroxylic hydrogen which stabilises the phenol, leaving the energy of the phenoxyl radical unaltered.Thus, solvation effects are expected to be large with unhindered phenols and relatively unimportant in phenols containing bulky substituents in the proximity of the OH group.
