title: Exploring the enantioseparation of amino-naphthol analogues by supercritical fluid chromatography.
abstract: The direct separation of the enantiomers of 1-(α-aminoarylmethyl)-2-naphthol, 1-(α-aminoalkyl)-2-naphthol, 2-(α-aminoarylmethyl)-1-naphthol analogues and 2-(1-amino-2-methylpropyl)-1-naphthol) was investigated in supercritical fluid chromatography. Five commercially available chiral stationary phases based on immobilized polysaccharide chiral selectors (Chiralpak IA, IB, IC, ID and IE) were evaluated. Chiralpak IB was by far the most efficient to achieve the separation of these racemates and was further selected for optimization of elution conditions. The effects of column temperature (varying between 5 and 45 °C) and co-solvent added to carbon dioxide (methanol, ethanol, isopropanol and dichloromethane) were investigated. A particular attention was paid to mobile-phase additives. Several of them, acids, bases or salts (namely water, formic acid, acetic acid, trifluoroacetic acid, diethylamine, diethanolamine, triethylamine, triethanolamine, dimethylethanolamine, ammonia and ammonium acetate), were tested in order to improve peak shapes while maintaining selectivity. With the help of other achiral naphthol derivatives, the additive effects were examined.
authors: Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary; University of Orleans, Institute of Organic and Analytical Chemistry (ICOA) , CNRS UMR 7311, Pôle de Chimie, rue de Chartres, 45067 Orleans Cedex 2, France.
authors: Anita
authors: A
authors: Aranyi
authors: Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary.
authors: István
authors: I
authors: Ilisz
authors: Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary.
authors: Antal
authors: A
authors: Péter
authors: Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary.
authors: Ferenc
authors: F
authors: Fülöp
authors: University of Orleans, Institute of Organic and Analytical Chemistry (ICOA) , CNRS UMR 7311, Pôle de Chimie, rue de Chartres, 45067 Orleans Cedex 2, France. Electronic address: caroline.west@univ-orleans.fr.
authors: Caroline
authors: C
authors: West
mesh_terms: D025924:Chromatography, Supercritical Fluid / Q000379:methods*; D009284:Naphthols / Q000737:chemistry / Q000302:isolation & purification*; D011134:Polysaccharides / Q000737:chemistry; D012492:Salts / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D009284:Naphthols; D011134:Polysaccharides; D012492:Salts; D012997:Solvents
keywords: Additives; Betti bases; Chiral stationary phases; Diethanolamine; Immobilized polysaccharide