A Comparative Study of Chromatographic Behavior and Lipophilicity of Selected Imidazoline Derivatives

Abstract

Chromatographic behavior and lipophilicity of 20 selected imidazoline derivatives were examined by thin-layer chromatography using CN, RP-2, RP-8 and RP-18 as the stationary phases and a mixture of methanol, water and ammonia as the mobile phase. In all examined chromatographic systems, linear relationships were established between retention parameters and the volume fraction of methanol in the mobile phase (r > 0.985, 0.978, 0.981, 0.988 for the CN, RP-2, RP-8 and RP-18, respectively). The highest correlation between the obtained R-M(0) values was observed for RP-2 and RP-8 stationary phases. The experimental lipophilicity indices (R-M(0), m and C-0) obtained from the retention data were used in correlation study with the calculated logP values. Experimentally determined R-M(0) values for all investigated chromatographic systems exhibited the highest correlation with the calculated ClogP values (r: 0.880, 0.872, 0.897 and 0.889 for the CN, RP-2, RP-8 and RP-18 stationary phases, respectively). In addition, principal component analysis enables new information about similarity and differences between tested compounds as well as experimental lipophilicity indices and calculated logP values. Performed QSRR analysis showed that the frequency of C-C at topological distance 1 and CATS2D Lipophilic-Lipophilic at lag 01 were important descriptors with influence on the R-M(0) values in all the examined chromatographic systems, while the differences in the retention behavior of compounds on the examined stationary phases can be distinguished based on their specific geometrical, electronic and constitutional properties.