English

Abstract

We report here the synthesis of phenyl(2 - phenyl - 2,3 - dihydro - 1H - perimidin - 2 - yl)methanone ( 2 ) by the condensation reaction between 1,8 - diaminonaphthalene ( 1 ) and benzil in equimolar ratio at ambient temperature. Further reaction of compound 2 with one equivalent of sodium borohydride at 0 oC resulted in quantitative conversion of ketone to corresponding alcohol, namely, phenyl(2 - phenyl - 2,3 - dihydro - 1H - perimidin - 2 - yl)methanol ( 3 ). The solid - state structures of both the compounds were established using single - crystal X - ray diffraction analysis. We probed, using quantum mechanics, the mechanism of formation of compound 2 through two of the most plausible routes and observed that it was more plausible that the first route, energy - wise, would result in product 2 . We also calculated the stabilization energy of intermolecular hydrogen bond ing, which leads to the formation of a dimer, which has already been observed in the solid - state structure of compound 3 .