Temperature-induced inversion of elution order in the chromatographic enantioseparation of 1,1'-bi-2-naphthol on an immobilized polysaccharide-based chiral stationary phase.
In this work, the enantioseparations of 1,1'-bi-2-naphthol (BINOL) and its three derivatives were performed on an immobilized polysaccharide-based chiral stationary phase, Chiralpak IA, under normal-phase mode. The effects of the content of polar modifier in the mobile phase and the column temperature on the retention and enantioseparation were investigated in detail. Temperature-induced inversion of elution order for BINOL was observed directly when n-hexane/2-propanol (92/8, v/v) was used as mobile phase. The isoenantioselective temperature (T(iso)) was calculated to be 31.4 degrees C. When n-hexane/2-propanol/THF (93/2/5, v/v/v) was used as mobile phase, the T(iso) value decreased to -8.2 degrees C. Entropically driven enantioseparation which had practical application was obtained successfully (separation factor being 1.189 and 1.332 at 25 degrees C and 50 degrees C, respectively). The corresponding thermodynamic parameters for other three binaphthyl compounds were compared with that for BINOL. Some inferences about chiral recognition mechanism were stressed.
Yao
Bixia
B
Department of Chemistry and Environmental Science, Zhangzhou Normal University, Zhangzhou 363000, China.
Zhan
Fengping
F
Yu
Guangyan
G
Chen
Zhifen
Z
Fan
Wenjing
W
Zeng
Xiongping
X
Zeng
Qingle
Q
Weng
Wen
W
D019840:2-Propanol / Q000737:chemistry; D002853:Chromatography, Liquid / Q000379:methods*; D005663:Furans / Q000737:chemistry; D006586:Hexanes / Q000737:chemistry; D009284:Naphthols / Q000737:chemistry / Q000302:isolation & purification*; D011134:Polysaccharides / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature; D013816:Thermodynamics
D005663:Furans; D006586:Hexanes; D009284:Naphthols; D011134:Polysaccharides; C026385:n-hexane; C018674:tetrahydrofuran; C412332:1,1'-bi-2-naphthol; D019840:2-Propanol