Quantitative analysis of molecular interaction potentials of ionic liquid anions using multi-functionalized...

The molecular interaction potentials, including S (dipolarity/polarizability), A (hydrogen bonding acidity), and B (hydrogen bonding basicity), of anions are experimentally determined using multi-functionalized stationary phases in high-performance liquid chromatography (HPLC) systems. We employ three different multi-functionalized stationary phase columns (Obelisc R, Obelisc N, and Acclaim Trinity-P1) combined with two ingredients, namely, acetonitrile (ACN) and methanol (MeOH). These conditions can cause neutral, cationic, and anionic compounds to be retained. By using the retention characteristics of calibration compounds, including cations, anions, and neutral compounds, system parameters including the ionic interaction terms (zc Zc , za Za ) are evaluated using multiple linear regression, resulting in a standard deviation (SD) of 0.090-0.158 log units. Based on the system parameters and retention characteristics of the anions of interest, their molecular interaction potentials are characterized on the same scale for neutral and cationic molecules. Furthermore, to verify the determined molecular interaction potentials, we predict anion hydrophobicity. The results show that the determined S, A, and B, together with the computable descriptors E (excess molar refraction) and V (McGowan volume), can predict anion hydrophobicity with R(2) =0.982 and SD=0.167 (dimensionless).