A DFT rationalization for the observed regiochemistry in the nitrile oxide cycloaddition with anthracene and acridine

A series of computational approaches, based on the global and local indexes defined in the context of the DFT, at the B3LYP/6-31G(d) computational level, were investigated to elucidate the regiochemistry and the energetics of the mesitonitrile oxide 1,3-dipolar cycloaddition with anthracene and the aza-analogue acridine. The results are in agreement with the observed regioselectivity and are in contrast with the ones predicted in terms of FMO theory.