Chromatographic optical resolution on trans-1,2-diaminocyclohexane derivatives: Theory and applications

An overall view on some new chiral stationary phases based on (trans)-1,2-diaminocyclohexane is illustrated. The selected chiral moiety, derivatized with different aroyl groups, has been linked to a silica matrix in order to give chiral stationary phases (CSPs) enabling them to be used efficiently in the normal and reverse phase, both for analytical and preparative purposes. In addition new polymeric CSPs have been prepared by using the same selector, suitably modified, as monomer. The new chiral stationary phases have been characterised by physicochemical methods and used for the resolution of various racemic compounds classes such as alpha-aryloxyacetic acids, alcohols, sulfoxides, selenoxides, phosphinates, tertiary-phosphine oxides, benzodiazepines etc. without prederivatization or as amines, amino acids, amino alcohols, nonsteroidal antiinflammatory agents in a derivatized form, The separated solutes structural variety suggests that multiple interaction sites are involved in the recognition process: some thermodynamic data relative to the CSPs-selectands interactions are also illustrated.