Computational Study of Aryl Transfer Mechanism from Oxygen toward Nitrogen Catalyzed by Acridinium Ion.

Benzene is an organic compound that exhibits uniqueness due to its aromaticity. The uniqueness of benzene results in the ubiquity of its derivatives, for example, Trp-Cage and a self-healing polymer. The reaction regarding of the aryl functional group tends to be difficult to occur because of the high energy requirement in the dearomatization process. In the presence of a photocatalyst, aryl migration is possible under relatively mild conditions. In this research, the mechanism of aryl transfer reaction from oxygen toward nitrogen of 2-phenoxyethane-1-amine to 2-(phenylamino)ethane-1-ol has been studied. The previously proposed mechanism is elucidated by using the density-functional theory (DFT) method. The proposed mechanism was partially refuted, and a new alternative is necessary regarding the proton transfer migration step. One of the alternative pathways is that the proton transfer is catalyzed by the reactant as described in the present work.