Abstract
The quantum chemical study on the reaction of phenol with formaldehyde was carried out. The molecular orbitals and energy levels were calculated at the B3LYP/6-31+G(d) level, using the conductor-like polarizable continuum model (CPCM) calculation. From the viewpoint of the frontier orbital theory, it was able to be specified the reactant chemical species in an acid- or in a base-catalyzed system. In the case of the reaction of phenol with formaldehyde, the calculated energy levels in gas-phase were insuficient, but the aqueous solvent modeling calculations by CPCM were reasonable for the frontier orbital theory. It was found that methylol cation reacts with phenol under acid catalyst, and phenolate reacts with formaldehyde under base catalyst. Furthermore, the reactivity of ortho and para position of phenol in an acid-catalyzed system was discussed. The energy transformation calculations suggested that the stability of the intermediate dominates the reactivity of ortho and para position of phenol.
