Computational and experimental studies of the conformational reactions of 1,3,5-tris(pentaphenylphenyl)benzene

Computational analyses of the five possible functional group rotations in 1,3,5-tris(pentaphenylphenyl)benzene (1) were conducted at three disparate levels of theory: AM1, HF/STO-3G, and B3LYP/6-31G(d). The ground state and transition state structures were located for all of the conformational reactions, and the free energies of activation for these processes were calculated. In addition, compound 1 was resolved by low-temperature chromatography on a chiral support, and its barrier to racemization was determined by dynamic chromatography. These computational and experimental results are compared with data from dynamic NMR studies of 1 in the literature.