Liquid chromatographic behavior of two alanine‐substituted calix[4]arene‐bonded silica gel stationary phases |
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Authors: | Zhifen Deng Junwei Liu Chenchen Hu Liu Yang Huifang Du Yanjie Huang Xiaoqing Yang Qiong Jiang Shusheng Zhang |
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Institution: | 1. Key Laboratory of Chemical Biology and Organic Chemistry of Henan, College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, P. R. China;2. Henan University of Traditional Chinese Medicine, Zhengzhou, P. R. China |
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Abstract: | Two new kinds of alanine‐substituted calix4]arene stationary phases of 5,11,17,23‐p‐tert‐butyl‐25,27‐bis(l ‐alanine‐methylester‐N‐carbonyl‐methoxy)‐26,28‐dihyroxycalix4]arene‐bonded silica gel stationary phase (BABS4) and 5, 11, 17, 23‐p‐tert‐butyl‐25,26,27,28‐tetra(l ‐alanine‐methylester‐N‐carbonyl‐methoxy)‐calix4]arene‐bonded silica gel stationary phase (TABS4) were prepared and characterized in the present study. They were compared with each other and investigated in terms of their chromatographic performance by using polycyclic aromatic hydrocarbons, disubstituted benzene isomers, and mono‐substituted benzenes as solute probes. The results indicated that both BABS4 and TABS4 exhibited multiple interactions with analytes. In addition, the commonly used Tanaka characterization protocol for the evaluation of commercially available stationary phases was applied to evaluate the properties of these two new functionalized calixarene stationary phases. The Tanaka test results were compared with Zorbax Eclipse XDB C18 and Kromasil phenyl columns, respectively. BABS4 has stronger hydrogen‐bonding capacity and ion‐exchange capacity than TABS4, and features weaker hydrophobicity and hydrophobic selectivity. Both of them behave similarly in stereoselectivity. Both BABS4 and TABS4 are weaker than C18 and phenyl stationary phases in hydrophobicity and hydrophobic selectivity. |
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Keywords: | Calix[4]arene stationary phases Chromatographic behavior Separation mechanisms Tanaka characterization protocol |
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