Structural and temperature effects in the high-performance liquid chromatographic enantioseparation of 1-(α-aminobenzyl)-2-naphthol and 2-(α-aminobenzyl)-1-naphthol analogs

• Published in: Journal of separation science 2005-12, Vol.28 (18), p.2505-2510
• Main Authors: SZTOJKOV-IVANOV, Anita, SZATMARI, Istvan, PETER, Antal, FüLÖP, Ferenc
• Format: Article
• Language: English
• Subjects: 1-(α-Aminobenzyl)-2-naphthol analogs; 2-(α-Aminobenzyl)-1-naphthol analogs; Analytical chemistry; Chemistry; Chemistry - methods; Chromatographic methods and physical methods associated with chromatography; Chromatography, High Pressure Liquid - methods; Enantiomer separation; Exact sciences and technology; Hot Temperature; HPLC; Models, Chemical; Naphthols - analysis; Naphthols - isolation & purification; Other chromatographic methods; Stereoisomerism; Temperature; Temperature effect; Thermodynamics
• ISSN: 1615-9306; 1615-9314
• DOI: 10.1002/jssc.200500138

The enantiomers of 1‐(α‐aminobenzyl)‐2‐naphthol and 2‐(α‐aminobenzyl)‐1‐naphthol analogs were separated isothermally on a cellulose‐tris‐3,5‐dimethylphenyl carbamate‐based chiral stationary phase (Chiralcel OD‐H), at 10°C increments in the range of 5–35°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, ln α, 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.