Discrimination between naphthacene and triphenylene using cellulose tris(4-methylbenzoate) and cellulose tribenzoate: A computational study

Abstract

The mechanisms of naphthacene and triphenylene discrimination using commercially available cellulose tris(4-methylbenzoate) (CMB) and cellulose tribenzoate (CB) chiral stationary phases were investigated using molecular mechanics calculations. Naphthacene and triphenylene could be separated by liquid chromatography on CMB and CB, with triphenylene being eluted earlier than naphthacene on both phases. However, the corresponding separation factor is much larger for CMB than for CB. The docking of these polycyclic aromatic hydrocarbons to the above polymers suggested that the most important sites of CMB and CB for interacting with these hydrocarbons are located at equivalent positions, featuring a space surrounded by main chain glucose units and benzoyl side chains. The difference of hydrocarbon stabilization energies with CMB and CB agreed well with the observed chromatographic separation factors.

Keywords: Cellulose tribenzoate; Cellulose tris(4-methylbenzoate); Grid search of docking; Liquid chromatography; Molecular mechanics calculation; Naphthacene.