QSRR Study on the Relationship between the Chromatographic Capacity Factor and Lipophilicity and Structure Parameters of Halogenated Thiophenols

The capacity factors (k') of fourteen types of halogenated thiophenols in different phases of methanol-water eluent were determined by reversed phased high-performance liquid chromatography (RP-HPLC) and the relationships between the logarithm of capacity factor lgK' and methanol ratio psi were analyzed. A fair linear relationship is found between lgK' and psi, and the correlation coefficients R-2 of the constructed linear equations are all greater than 0.990. Relationship between the chromatographic data lgK(w) when extrapolated to pure water and n-octanol/water partition coefficient lgK(ow) obtained by the group contribution method has shown a good linear correlation with R-2 = 0.956. The structure parameters of fourteen halogenated thiophenols were calculated by using DFT, and the correlation equation of lgK(w)' and structure parameters was obtained by using SPSS, lgK(w)' = -0.409 + 0.039 alpha and R-2 = 0.981, meaning that lgK(w)' is mainly determined by the polarizability alpha.