Summary
Various benzimidazole sulphoxides were chirally resolved employing an amylase-based chiral stationary phase. The structure-property relationships of these compounds were investigated using calculated physico-chemical properties, molecular modelling and multivariate statistical techniques. A data set of 254 molecular descriptors was used to represent the series of compounds. Analysis of the data set using principal components analysis and non-linear mapping suggested that the separation factor of each enantiomeric pair was associated with nine molecular properties and, in particular, molar refractivity of the Z substituent and the partial charge of atom 6. The separation factor of a sulphoxide not used in the analysis was well predicted thus suggesting that these models may be used to generalize.
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Camilleri, P., Livingstone, D.J., Murphy, J.A. et al. Chiral chromatography and multivariate quantitative structure-property relationships of benzimidazole sulphoxides. J Computer-Aided Mol Des 7, 61–69 (1993). https://doi.org/10.1007/BF00141575
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DOI: https://doi.org/10.1007/BF00141575