Assessment of chromatographic lipophilicity of some anhydro-D-aldose derivatives on different stationary phases by QSRR approach

Abstract

Copyright © Taylor & Francis Group, LLC. This study is based on the analysis of the retention behavior of some anhydro-D-aldose derivatives in reversed-phase thin-layer chromatography (RP-TLC). Chromatographic separations were achieved applying a methanol/water mobile phase and three different stationary phases: C18-bonded silica gel, silica gel impregnated with paraffin oil, and silica gel impregnated with squalane. Retention behavior of the analyzed molecules was defined by RM0 constant and correlated with in silico molecular descriptors. According to the statistical validation parameters, obtained results showed that the established multiple-linear quantitative structure-retention relationship models (MLR-QSRR) can successfully predict the chromatographic lipophilicity of structurally similar compounds. In the present study the influence of some functional groups on the total lipophilicity of studied derivatives was determined as well. Principal component analysis (PCA) was applied in order to obtain an overview of similarity or dissimilarity among the analyzed compounds and hierarchical cluster analysis (HCA) was applied in order to compare separation characteristics of the applied stationary phases.