Gas-phase thermochemical properties of some tri-substituted phenols: A density functional theory study
Miranda, MS; Esteves da Silva, JCG; Liebman, JF
| HERO ID | 2908022 |
|---|---|
| In Press | No |
| Year | 2015 |
| Title | Gas-phase thermochemical properties of some tri-substituted phenols: A density functional theory study |
| Authors | Miranda, MS; Esteves da Silva, JCG; Liebman, JF |
| Journal | Journal of Chemical Thermodynamics |
| Volume | 80 |
| Page Numbers | 65-72 |
| Abstract | The study of the energetics of phenolic compounds has a considerable practical interest since this family of compounds includes numerous synthetic and naturally occurring antioxidants. In this work, density functional theory (DFT) has been used to investigate gas-phase thermochemical properties of the following tri-substituted phenols: 2,4,6-trimethylphenol, 2,6-dimethyl-4-tert-butylphenol, 2, 6-dimethyl-4-methoxyphenol, 2,4,6-tri-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol, 2,6-di-tertbutyl-4-methoxyphenol, 2,4,6-trimethoxyphenol, 2,6-dimethoxy-4-methylphenol and 2,6-dimethoxy-4-tert-butylphenol. Molecular structures were computed with the B3LYP and the omega B97X-D functionals and the 6-31G(d) basis set. More accurate energies were obtained from single-point energy calculations with both functionals and the 6-311++G(2df,2pd) basis set. Standard enthalpies of formation of the phenolic molecules and phenoxyl radicals were derived using an appropriate homodesmotic reaction. The O-H homolytic bond dissociation enthalpies, gas-phase acidities and adiabatic ionization enthalpies were also calculated. The general good agreement found between the calculated and the few existent experimental gas-phase thermochemical parameters gives confidence to the estimates concerning the phenolic compounds which were not yet experimentally studied. (C) 2014 Elsevier Ltd. All rights reserved. |
| Doi | 10.1016/j.jct.2014.08.025 |
| Wosid | WOS:000344019500009 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | Tri-substituted phenols; Molecular structure; Enthalpy of formation; O-H homolytic bond dissociation enthalpy; Acidity; Adiabatic ionization enthalpy |