Structural and temperature effects in the high-performance liquid chromatographic enantioseparation of 1-(alpha-aminobenzyl)-2-naphthol and 2-(alpha-aminobenzyl)-1-naphthol analogs.
The enantiomers of 1-(alpha-aminobenzyl)-2-naphthol and 2-(alpha-aminobenzyl)-1-naphthol analogs were separated isothermally on a cellulose-tris-3,5-dimethylphenyl carbamate-based chiral stationary phase (Chiralcel OD-H), at 10 degrees C increments in the range of 5-35 degrees C, using n-hexane/2-propanol/diethylamine as mobile phase. The mobile phase composition and temperature were varied to achieve baseline resolutions in a single chromatographic run. The dependence of the natural logarithms of selectivity factors, In alpha, on the inverse of temperature, 1/T, was used to determine the thermodynamic data of the enantiomers. The thermodynamic data revealed that all the compounds in this study separate via the same enthalpy-driven chiral recognition mechanism.
Sztojkov-Ivanov
Anita
A
Institute of Pharmaceutical Chemistry, University of Szeged, Szeged, Hungary.
Szatmári
István
I
Péter
Antal
A
Fülöp
Ferenc
F
D002621:Chemistry / Q000379:methods; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D006358:Hot Temperature; D008956:Models, Chemical; D009284:Naphthols / Q000032:analysis* / Q000302:isolation & purification*; D013237:Stereoisomerism; D013696:Temperature; D013816:Thermodynamics
D009284:Naphthols; C090659:1-amino-2-naphthol