An theoretical investigation of reaction site of 2,4′,6-trifluorobenzophenone, 2,4′,6-trifluorophenylsulfone with hydroquinone

A detailed theoretical study for the nucleophilic aromatic substitution reaction of 2,4′,6-trifluorobenzophenone (TF), 2,4′,6-trifluorophenylsulfone (TFS) with hydroquinone was performed at the density function theory level together with the polarizable continuum model. With detailed free energy profiles and transition state structures, our theoretical study confirms that TF or TFS with the para-position fluorine has more thermodynamic and kinetic advantages than that with the ortho-position fluorine. In addition, the calculations involving the local reactivity indices (Fukui function), the global reactivity indices (electronic chemical potential), and rate constants further corroborate the location of the preferred bonding site. The impacts of resonance effect, introductive effect, and steric effect were comprehensively considered to explain the reason why para-position is a good reaction site. Our computational results are in good agreement with experimental results and give the potential polymer materials TFS.