Theoretical Study on the Properties of Phenol and its Ozonide

Adopting BYLP method in Density Functional Theory (DFT), we make theoretical study on the ozonide-orthophenylphenol, parachlorophenol, orthobenzoquinone and parabenzoquinone in the two reaction routes of phenol oxidizing into benzoquinone with ozone. We get the geometric configuration of molecules, charge distribution of atoms, thermodynamical properties and frontier orbit energy. Natural Bond Orbital(NBO)charge calculation shows that compared with orthobenzoquinone and parabenzoquinone molecules, phenol, orthophenylphenol and parachlorophenol molecules have stronger reactivity and they are more likely to have electrophilic substitution reaction. Thermodynamic properties indicate that phenol is easy to have oxidation reaction and produce orthophenylphenol which is easily to oxidize into orthobenzoquinone no matter at low temperature, room temperature or high temperature. Another reaction pathwaycalculation shows that in thermodynamics, phenol will not easily ozonize into parachlorophenol; while parachlorophenol will easily ozonize into parabenzoquinone. Frontier orbit energy calculation shows that phenol, orthophenylphenol, and parachlorophenol show similar stability. Orthobenzoquinone and parabenzoquinone have the strongest stability.