Regular ArticleThermochemistry of phenols: experimental standard molar enthalpies of formation of 2-phenylphenol, 4-phenylphenol, 2,6-diphenylphenol, and 2,2′- and 4,4′-dihydroxybiphenyl
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Mechanistic and kinetic insights into phenol-catalyzed cyclotrimerization of cyanate esters
2022, Thermochimica ActaThermochemistry of di-substituted benzenes: Ortho-, meta-, and para-hydroxyacetophenones
2020, Journal of Chemical ThermodynamicsCitation Excerpt :To our surprise, thermochemical information about these compounds is quite restricted [2–11]. This paper extends our previous studies [12–21] on the systematic investigation of substituent effects of hydroxyl group on the benzene ring. We report here determination of vapour pressures and vapourisation or sublimation enthalpies of a series of ortho-, meta-, and para-hydroxyacetophenones (see Fig. 1).
Thermodynamic properties of glycerol: Experimental and theoretical study
2015, Fluid Phase EquilibriaGas-phase thermochemical properties of some tri-substituted phenols: A density functional theory study
2015, Journal of Chemical ThermodynamicsCitation Excerpt :Synthetic phenolic compounds such as 2,6-di-tert-butyl-4-methylphenol (known as BHT) and 2,6-di-tert-butyl-4-methoxyphenol (known as DBHA) provide a vital defense against unwanted air-derived oxidation (autooxidation) in commercial products [3]. Although a considerable effort has been made in the last decades for the measurement of the enthalpies of formation of phenolic compounds [4–33] and OH bond dissociation enthalpies (see reviews of literature data in references [34,35]), values of these parameters for many important tri-substituted phenols are still missing, as well as other thermodynamic parameters namely enthalpies of formation of phenoxyl radicals, gas-phase acidities and adiabatic ionization enthalpies. In this work we have investigated, using density functional theory (DFT) at the B3LYP/6-311++G(2df,2pd)//B3LYP/6-31G(d) and ωB97X-D/6-311++G(2df,2pd)//ωB97X-D/6-31G(d) levels, several gas-phase thermochemical properties namely enthalpies of formation, OH homolytic bond dissociation enthalpies, gas-phase acidities and adiabatic ionization enthalpies of the following tri-substituted phenols: 2,4,6-trimethylphenol (2,4,6-Me3C6H2OH), 2,6-dimethyl-4-tert-butylphenol (2,6-Me2-4-tBuC6H2OH), 2,6-dimethyl-4-methoxyphenol (2,6-Me2-4-MeOC6H2OH), 2,4,6-tri-tert-butylphenol (2,4,6-tBu3C6H2OH), 2,6-di-tert-butyl-4-methylphenol (2,6-tBu2-4-MeC6H2OH), 2,6-di-tert-butyl-4-methoxyphenol (2,6-tBu2-4-MeOC6H2OH), 2,4,6-trimethoxyphenol (2,4,6-(MeO)3C6H2OH), 2,6-dimethoxy-4-methylphenol (2,6-(MeO)2-4-MeC6H2OH) and 2,6-dimethoxy-4-tert-butylphenol (2,6-(MeO)2-4-tBuC6H2OH).
Prediction of vapor pressures of solid organic compounds with a group-contribution method
2003, Fluid Phase Equilibria
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The experimental part of this work was done at the Institute of Organic Chemistry and Biochemistry, University of Freiburg, F.R.G. (E-mail: [email protected]).