Temperature-induced inversion of elution order in the chromatographic enantioseparation of 1,1'-bi-2-naphthol on an immobilized polysaccharide-based chiral stationary phase.
作者： Bixia Yao , Fengping Zhan , Guangyan Yu , Zhifen Chen , Wenjing Fan
DOI: 10.1016/J.CHROMA.2009.05.032
关键词:
摘要: 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 content polar modifier in mobile phase column temperature retention enantioseparation investigated detail. Temperature-induced inversion elution order for BINOL was observed directly when n-hexane/2-propanol (92/8, v/v) used as phase. isoenantioselective (T(iso)) calculated to be 31.4 degrees C. When n-hexane/2-propanol/THF (93/2/5, v/v/v) T(iso) value decreased -8.2 Entropically driven which had practical application obtained successfully (separation factor being 1.189 1.332 at 25 C 50 C, respectively). corresponding thermodynamic parameters other binaphthyl compounds compared with that BINOL. Some inferences about recognition mechanism stressed.
elsevier.com
sci-hub.se 参考文章(25)
Tong Zhang, Dung Nguyen, Pilar Franco, Tatsushi Murakami, Atsushi Ohnishi, Hidehiro Kurosawa, Cellulose 3,5-dimethylphenylcarbamate immobilized on silica Analytica Chimica Acta. ,vol. 557, pp. 221- 228 ,(2006) , 10.1016/J.ACA.2005.10.017
Mickael Michaud, Eric Jourdan, Corinne Ravelet, Annick Villet, Anne Ravel, Catherine Grosset, Eric Peyrin, Immobilized DNA aptamers as target-specific chiral stationary phases for resolution of nucleoside and amino acid derivative enantiomers. Analytical Chemistry. ,vol. 76, pp. 1015- 1020 ,(2004) , 10.1021/AC035090F
Rodger W. Stringham, John A. Blackwell, Factors That Control Successful Entropically Driven Chiral Separations in SFC and HPLC. Analytical Chemistry. ,vol. 69, pp. 1414- 1420 ,(1997) , 10.1021/AC9609283
Volker Schurig, Joachim Ossig, Rainer Link, Evidence for a Temperature Dependent Reversal of the Enantioselectivity in Complexation Gas Chromatography on Chiral Phases Angewandte Chemie. ,vol. 28, pp. 194- 196 ,(1989) , 10.1002/ANIE.198901941
William H. Pirkle, Patrick G. Murray, An instance of temperature-dependent elution order of enantiomers from a chiral brush-type HPLC column Hrc-journal of High Resolution Chromatography. ,vol. 16, pp. 285- 288 ,(1993) , 10.1002/JHRC.1240160505
Katrin Fulde, August Wilhelm Frahm, Temperature-induced inversion of elution order in the enantioseparation of sotalol on a cellobiohydrolase I-based stationary phase. Journal of Chromatography A. ,vol. 858, pp. 33- 43 ,(1999) , 10.1016/S0021-9673(99)00798-0
T. O'Brien, L. Crocker, R. Thompson, K. Thompson, P. H. Toma, D. A. Conlon, B. Feibush, C. Moeder, G. Bicker, N. Grinberg, Mechanistic aspects of chiral discrimination on modified cellulose. Analytical Chemistry. ,vol. 69, pp. 1999- 2007 ,(1997) , 10.1021/AC961241L
Tong Zhang, Dung Nguyen, Pilar Franco, Enantiomer resolution screening strategy using multiple immobilised polysaccharide-based chiral stationary phases. Journal of Chromatography A. ,vol. 1191, pp. 214- 222 ,(2008) , 10.1016/J.CHROMA.2007.12.026
Wen Weng, Hongxu Guo, Fengping Zhan, Hongli Fang, Qingxiang Wang, Bixia Yao, Shunxing Li, Chromatographic enantioseparations of binaphthyl compounds on an immobilized polysaccharide-based chiral stationary phase. Journal of Chromatography A. ,vol. 1210, pp. 178- 184 ,(2008) , 10.1016/J.CHROMA.2008.09.048
Wen Weng, Qingle Zeng, Bixia Yao, Qinghua Wang, Saiqing Li, Influence of Mobile Phase Composition on the Apparent Thermodynamic Characteristics in Liquid Chromatographic Enantioseparation on a Tartardiamide-Based Stationary Phase Chromatographia. ,vol. 61, pp. 561- 566 ,(2005) , 10.1365/S10337-005-0560-5