Multiequilibria of 2-(2’-furanyl)-1H-Benzimidazole Neutral and Protonated Forms in the Presence of Amphiphilic Aggregates

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Abstract

The solubility of 2-(2’-furanyl)-lH-benzimidazole (Fuberidazole) in water-surfactant systems is measured as a function of the pH. The partition constants between water and the micellar pseudophase of both neutral and protonated forms of Fuberidazole (pKal = 5.0) are determined in buffered solutions of an anionic surfactant, sodium dodecyl sulfate (SDS), a cationic surfactant, hexadecyltrimethylammonium chloride (HTAC), and a nonionic surfactant, polyoxyethylene( 10) lauryl ether (C12E10) using the fluorescence anisotropy method, and the results compared with those obtained for the octanol-water system. Both forms of Fuberidazole are shown to dissolve readily in the polyoxyethylene region of the ClzElo micelles, with partition constants of 190 f 20 and 3.8 f 0.2 at 25 “C for the neutral and protonated forms, respectively. In SDS, much higher values of the partition constants are observed, respectively, 310 f 25 and 11 600 f 1O00, presenting a very low temperature dependence. As expected, the cation is not soluble in HTAC micelles, but the neutral form presents a high partition constant of 850 f 80. Finally, we discuss the partition of Fuberidazole and protonated Fuberidazole between micelle and water as a function of the volume fraction of lipidic media, for different pH values.
Original languageEnglish
Pages (from-to)2448-2453
Number of pages6
JournalEnvironmental Science and Technology
Volume26
Issue number12
DOIs
Publication statusPublished - 1992

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