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首页> 美国卫生研究院文献>Molecules >Enantioseparation of 55′-Dibromo-22′-dichloro-3-selanyl-44′-bipyridines on Polysaccharide-Based Chiral Stationary Phases: Exploring Chalcogen Bonds in Liquid-Phase Chromatography
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Enantioseparation of 55′-Dibromo-22′-dichloro-3-selanyl-44′-bipyridines on Polysaccharide-Based Chiral Stationary Phases: Exploring Chalcogen Bonds in Liquid-Phase Chromatography

机译：55-二溴-22-二氯-3-硒基-44-双吡啶对基于多糖的手性静止阶段的映对解性：液相色谱中的硫致原键

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The chalcogen bond (ChB) is a noncovalent interaction based on electrophilic features of regions of electron charge density depletion (σ-holes) located on bound atoms of group VI. The σ-holes of sulfur and heavy chalcogen atoms (Se, Te) (donors) can interact through their positive electrostatic potential (V) with nucleophilic partners such as lone pairs, π-clouds, and anions (acceptors). In the last few years, promising applications of ChBs in catalysis, crystal engineering, molecular biology, and supramolecular chemistry have been reported. Recently, we explored the high-performance liquid chromatography (HPLC) enantioseparation of fluorinated 3-arylthio-4,4′-bipyridines containing sulfur atoms as ChB donors. Following this study, herein we describe the comparative enantioseparation of three 5,5′-dibromo-2,2′-dichloro-3-selanyl-4,4′-bipyridines on polysaccharide-based chiral stationary phases (CSPs) aiming to understand function and potentialities of selenium σ-holes in the enantiodiscrimination process. The impact of the chalcogen substituent on enantioseparation was explored by using sulfur and non-chalcogen derivatives as reference substances for comparison. Our investigation also focused on the function of the perfluorinated aromatic ring as a π-hole donor recognition site. Thermodynamic quantities associated with the enantioseparation were derived from van’t Hoff plots and local electron charge density of specific molecular regions of the interacting partners were inspected in terms of calculated V. On this basis, by correlating theoretical data and experimental results, the participation of ChBs and π-hole bonds in the enantiodiscrimination process was reasonably confirmed.
机译：硫属元素键（CHB）是基于位于VI族结合原子的电子电荷密度耗竭（σ-孔）的电泳特征的非共价相互作用。硫和重硫致原子（SE，TE）（供体）的σ-孔可以通过它们的正静电电位（V）与亲核伴侣相互作用，例如孤立对，π云和阴离子（受体）。在过去几年中，已经报道了CHB在催化作用，水晶工程，分子生物学和超分子化学中的有希望的应用。最近，我们探讨了含氟原子作为CHB供体的氟原子的高效液相色谱（HPLC）映射分离的氟化3-芳硫基-4,4'-苯乙烯。在本研究之后，在本文中，我们描述了三种5,5'-二溴-2,2'-二氯-3-硒基-4,4'-双吡啶对旨在理解功能的基于多糖的手性固定阶段（CSP）的比较映对分析硒Σ-孔的潜在能力在映染色过程中。通过使用硫和非硫芥子衍生物作为参考物质，探索了硫代原取代基对对映的对映的映映的影响进行了比较。我们的研究还集中于全氟化芳环的功能作为π孔仪识别部位。与对映的热力学的热力学量来自于Vane'tHoff图中，在计算的V.根据理论数据和实验结果相关，参与在映染色过程中的CHB和π孔键合理确认。

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