Chromatographic resolution on methylbenzoylcellulose beads: Modulation of the chiral recognition by variation of the position of the methyl group on the aromatic ring

Abstract

The preparation of cellulose-based chiral stationary phases (CSPs) in the pure polymer from ( i.e., without an achiral support such as silica gel), according to a process already reported for benzoyl cellulose, was extended to substituted benzoylcellulose derivatives. The chiral recognition abilities of benzoylcellulose and o-, m- and p-methylbenzoylcellulose were compared. The four CSPs are shown to exhibit different selectivites and in numerous instances an inversion of the elution order was observed on the different methylbenzoylcellulose CSPs, indicating that the CSPs undergo different interactions with the same racemic solute. The broad variety of racemic structures that can be resolved on the four CSPs indicate the great application potential of the new cellulose-based sorbents. This should be the case especially for preparative separations, as the materials are not deposited on an achiral supporting matrix and thus have a higher loading capacity than coated CSPs.