title: Investigation on the preparation and chromatographic behavior of a new para-tert-butylcalix[4]arene-1,2-crown-4 stationary phase for high performance liquid chromatography.
abstract: In the present work, a new para-tert-butylcalix[4]arene-1,2-crown-4 bonded silica stationary phase (CBS4-4) was synthesized, structurally characterized, and employed to separate polycyclic aromatic hydrocarbons (PAHs), phenols, aromatic amines, benzoic acid and its derivatives. The chromatographic behaviors of the prepared stationary phase were investigated and compared with ODS. The effects of methanol concentrations on the retention index show that CBS4-4 exhibits high selectivity for the above analytes. The separation mechanisms based on the different interactions between calixarene and the analytes were discussed. With the assistance of quantum chemistry calculation, the interaction Gibbs free energy change ΔG(solv) (in the mobile phase) of p, m and o-phenylenediamine positional isomers and para-tert-butylcalix[4]arene-1,2-crown-4 were obtained. The ΔG(solv) values were consistent with the retention behavior of p, m and o-phenylenediamine on the CBS4-4. According to the chromatographic data, it can be concluded that the selectivity of CBS4-4 for analytes is mainly ascribed to hydrophobic interaction, accompanied by other effects such as hydrogen bonding interaction, π-π and inclusion interaction. The CBS4-4 column has been successfully employed for the analysis of benzoic acid in Sprite drink.
authors.affiliation: Chemistry Department, Key Laboratory of Chemical Biology and Organic Chemistry of Henan, Zhengzhou University, Zhengzhou 450052, PR China.
authors.forename: Kai
authors.initials: K
authors.lastname: Hu
authors.forename: Wenjie
authors.initials: W
authors.lastname: Zhao
authors.forename: Fuyong
authors.initials: F
authors.lastname: Wen
authors.forename: Junwei
authors.initials: J
authors.lastname: Liu
authors.forename: Xiaolan
authors.initials: X
authors.lastname: Zhao
authors.forename: Zhanhui
authors.initials: Z
authors.lastname: Xu
authors.forename: Bailin
authors.initials: B
authors.lastname: Niu
authors.forename: Baoxian
authors.initials: B
authors.lastname: Ye
authors.forename: Yangjie
authors.initials: Y
authors.lastname: Wu
authors.forename: Shusheng
authors.initials: S
authors.lastname: Zhang
mesh_terms: D047250:Calixarenes / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D043844:Crown Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D057927:Hydrophobic and Hydrophilic Interactions; D007202:Indicators and Reagents; D013816:Thermodynamics
chemical_list: D043844:Crown Ethers; D007202:Indicators and Reagents; D047250:Calixarenes