Standard enthalpies of formation of 2,6-di-tert-butyl-4-methylphenol and 3,5-di-tert-butylphenol and their phenoxy radicals

The standard (p(o) = 0.1 MPa) enthalpies of formation of 2,6-di-tert-butyl- 4-methylphenol and 3,5-di-tert-butylphenol in the gaseous phase, -315.5 +/- 4.4 kJ mol(-1) and -312.7 +/- 4.6 kJ mol(-1), respectively, were derived f rom the standard enthalpies of combustion, in oxygen, at 298.15 K, measured by static bomb combustion calorimetry, and from the standard enthalpies of sublimation, at 298.15 K, measured by Calvet microcalorimetry. The O-H bon d dissociation enthalpies in those compounds were determined in benzene by photoacoustic calorimetry, leading to the standard enthalpies of formation of the gaseous phenoxy radicals: -189 +/- 8 kJ mol(-1) and -154 +/- 6 kJ mo l(-1), respectively. These results were used to calculate enthalpies of sub stituent redistribution reactions, which are proposed as a method to estima te new data for substituted phenols.