The effect of the ionic liquids’ nature on sorption of the benzimidazole and some of its derivatives from aqueous-acetonitrile solutions on octadecyl silica gel
Abstract
The study of the sorption of biologically active compounds (BAC) from liquid solutions is an im-portant area of modern science and practice, as it concerns a lot of areas of human activity, such as ecology and medicine. The BAC are potential active components of drugs, therefore the study of their sorption could be useful in solving problem of pharmaceutical quality control, the development of Russian analogues of for-eign drugs, as well as the problem of purifying natural reservoirs and waste waters. The most appropriate method for the research of drugs is reversed-phase high-performance liquid chromatography (RP HPLC). However, a number of problems arise in BAC studies by RP HPLC, such as, protein denaturation, the com-plexity of separating drug mixtures, and the problem of a strong dependence of retention factors on the surface characteristics of a particular sorbent. The ionic liquids (IL) could be a possible solution to this problem, as due to their dual nature, they could support a number of intermolecular interactions important for chromatog-raphy both with the sorbent surface and with analytes, which makes them promising additives in RP HPLC.
Therefore, the aim of this research was to study the effect of the nature of IL on the retention of benzimidazole and its derivatives synthesized for the first time from aqueous acetonitrile eluents and eluents containing dissolved 1-butyl-2,3-dimethylimidazolium tetrafluoroborate ([BdMIM] [BF4]) or 1 -butyl-3-me-thylimidazolium bromide ([BMIM] [Br]). The effect of the composition of aqueous acetonitrile solution on the retention factors of benzimidazole derivatives on octadecyl silica gel was considered within Snyder-Socze-wiński and Soczewiński–Wachtmeister models, and the corresponding slopes ratios were calculated. It was shown that the dependences for some sorbates are not linear. Consequently, their retention could not be de-scribed by used semiempirical models.
Comparing the slope ratios of the Soczewiński-Wachtmeister and Snyder-Soczewiński equations, it was shown that both the nature of ionic liquids and the structure of the analysed compounds affect the complex of intermolecular interactions. It was revealed that the system with [[BdMIM][BF4] is characterized by the lowest values of n and S for all compounds. Also it was shown that in this system the Soczewiński–Wachtmeister and Snyder-Soczewiński models could not describe the retention of the following sorbates: benzimidazole (sorbate no. 1), 1,2 bis (hydroxymethyl) benzimidazole (sorbate no. 3); and 2-benzyl-1-(3-phenylpropyl)-1H-benzim-idazole (sorbate no. 6).
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