title: Effects of organic modifier and temperature on the enantiomeric separation of several azole drugs using supercritical fluid chromatography and the Chiralpak AD column.
abstract: The effects of organic modifier and temperature on the enantioseparation of 10 triazoles and eight imidazoles, using supercritical fluid chromatography with the Chiralpak AD column, have been investigated in this work. For this purpose four different organic modifiers (methanol, ethanol, 2-propanol and acetonitrile) were evaluated. Only in the case of two compounds could the enantiomeric separation not be achieved with any of the modifiers tested; the rest of compounds were baseline or partially resolved with at least one of the modifiers. The alcohol-type modifiers provided the best results in terms of retention time and resolution. In general, retention increased in the order methanol < ethanol < 2-propanol; moreover it was possible to establish a relationship between the retention and the number of aromatic rings and dioxolane groups in the molecule, that is, the higher the number is, the higher the retention time. From the study of the temperature effect, the enthalpy-entropy compensation was demonstrated for all the compounds, except for bifonazole using methanol and miconazole using acetonitrile. This suggested that both analytes are enantiomerically resolved through different mechanisms.
authors.affiliation: I.U. CINQUIMA, Analytical Chemistry Group, University of Valladolid, E-47011, Valladolid, Spain.
authors.forename: L
authors.initials: L
authors.lastname: Toribio
authors.forename: J L
authors.initials: JL
authors.lastname: Bernal
authors.forename: M T
authors.initials: MT
authors.lastname: Martín
authors.forename: J
authors.initials: J
authors.lastname: Bernal
authors.forename: M J
authors.initials: MJ
authors.lastname: Del Nozal
mesh_terms: D000688:Amylose / Q000031:analogs & derivatives / Q000737:chemistry; D001393:Azoles / Q000737:chemistry* / Q000302:isolation & purification*; D025924:Chromatography, Supercritical Fluid / Q000295:instrumentation / Q000379:methods*; D015394:Molecular Structure; D004364:Pharmaceutical Preparations / Q000737:chemistry* / Q000302:isolation & purification*; D048448:Phenylcarbamates / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D001393:Azoles; D004364:Pharmaceutical Preparations; D048448:Phenylcarbamates; C080033:Chiralpak AD; D000688:Amylose
keywords: Chiralpak AD; SFC; chiral separation; imidazoles and triazoles; modifier effect; temperature effect