In-depth characterization of six cellulose tris-(3,5-dimethylphenylcarbamate) chiral stationary phases in supercritical fluid chromatography

摘要

Since the expiration of the patent protection of Chiralcel OD, similar chiral stationary phases (CSPs), all based on the same chiral selector, have been introduced on the market with the promise to reproduce or improve the performance of the original cellulose tris-(3,5-dimethylphenylcarbamate) CSP. We report here-in an in-depth evaluation of four generic versions of Chiralcel OD (CelluCoat, RegisCell, Lux Cellulose-1, Reprosil-OM) and the immobilized version (Chiralpak IB) in comparison to the original Chiralcel OD in terms of retention and enantioselectivity, with the help of chemometrics. First of all, the CSPs are compared based on the retentions of 230 achiral compounds. Agglomerative hierarchical clustering and quantitative structure-retention relationships based on a modified version of the solvation parameter model are used to assess the differences in non-enantioselective interactions contributing to retention. Secondly, the CSPs are compared based on the separation factors measured for 130 racemates. Discriminant analysis is then used to unravel the structural features contributing to the successful enantioselective separations. Chiralcel OD is shown to be the most versatile of the six tested CSPs, and involves a unique and unequalled mechanism to achieve enantioseparation.