title: High-performance liquid chromatographic enantioseparation of 1-(phenylethylamino)- or 1-(naphthylethylamino)methyl-2-naphthol analogs and a temperature-induced inversion of the elution sequence on polysaccharide-based chiral stationary phases.
abstract: The stereoisomers of five 1-(phenylethylamino)methyl-2-naphthol analogs or 1-(naphthylethylamino)methyl-2-naphthol analogs containing two chiral centers were directly separated on chiral stationary phases containing the chiral selectors cellulose tris-(3,5-dimethylphenyl) carbamate (Lux Cellulose-1), cellulose tris-(3-chloro-4-methylphenyl) carbamate (Lux Cellulose-2) and amylose tris-(5-chloro-2-methylphenyl) carbamate (Lux Amylose-2). Experiments were performed in normal-phase mode in a wide temperature range -5 to 70°C. Thermodynamic parameters and T(iso) values were calculated from plots of lnk or lnα vs. 1/T. -Δ(ΔH°) ranged from 1.0 to 4.7 kJ mol(-1), -Δ(ΔS°) from 1.6 to 11.0 J mol(-1) K(-1) and -Δ(ΔG°) from 0.1 to 1.5 kJ mol(-1). The sequence of elution of the stereoisomers was determined in all cases and in one case a temperature-induced inversion of the elution sequence was observed.
authors.affiliation: Department of Inorganic and Analytical Chemistry, University of Szeged, Szeged, Hungary.
authors.forename: Anita
authors.initials: A
authors.lastname: Aranyi
authors.forename: István
authors.initials: I
authors.lastname: Ilisz
authors.forename: Zoltán
authors.initials: Z
authors.lastname: Pataj
authors.forename: István
authors.initials: I
authors.lastname: Szatmári
authors.forename: Ferenc
authors.initials: F
authors.lastname: Fülöp
authors.forename: Antal
authors.initials: A
authors.lastname: Péter
mesh_terms: D000688:Amylose / Q000031:analogs & derivatives; D002482:Cellulose / Q000031:analogs & derivatives* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D009284:Naphthols / Q000737:chemistry / Q000302:isolation & purification*; D010627:Phenethylamines / Q000737:chemistry / Q000302:isolation & purification*; D048448:Phenylcarbamates / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D009284:Naphthols; D010627:Phenethylamines; D048448:Phenylcarbamates; D002482:Cellulose; D000688:Amylose