RESUMO
The retention of 16 quinoline and tetrahydroquinoline derivatives was investigated under liquid chromatography conditions using porous graphitized carbon (PGC), octadecyl silica (ODS) and hypercrosslinked polystyrene (HCLP) stationary phases. For most of the analytes, retention on PGC was greater than on ODS, while retention on HCLP was even greater than on both ODS and PGC. The non-linearity of retention dependencies on acetonitrile content in the eluent was observed for compounds containing carboxy, hydrazo and methoxy groups. The relationships between quinolines structure and their retention factors were investigated. It was found that sorption on different sorbents correlated with different descriptors. Retention on ODS was found to be highly correlated with lipophilicity only while on HCLP it depended on both lipophilicity and polarizability of the sorbates. The feature of PGC was a good correlation of retention factors with topological and geometrical parameters. Additionally, ability of PGC to form OH π bonds with hydroxymethylquinolines was found. The observed regularities allow one to rationally optimize the chromatographic analysis of structurally similar compounds, which is very important for bioactive substances.
RESUMO
The aim of our study was to investigate relationships between quinoline derivatives structure and their retention under reversed-phase liquid chromatography conditions. Retention factors of quinolines were experimentally measured and various geometrical and physicochemical parameters representing analytes molecular structure were calculated. Equations connecting chromatographic data with computed characteristics for the set of 17 investigated compounds were constructed. It was shown that the most precise dependencies include combination of physico-chemical and geometrical parameters.
