Chiral Self-Selectivity in Two Model Dinitrobenzoyl-Derivatized Brush-Type Chiral Stationary Phases

Chiral Self-Selectivity in Two Model Dinitrobenzoyl-Derivatized Brush-Type Chiral Stationary Phases
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两种模型二硝基苯甲酰衍生刷型手性固定相的手性自选择性

DOI:
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发表时间:
2009
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通讯作者:
J. Hugh Horton
J. Hugh Horton
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文献类型:
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作者:
S. Nita;J. Hugh Horton

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研究了N-(3,5-二硝基苯甲酰基)苯甘氨酸和N-(3,5-二硝基苯甲酰基)亮氨酸两种模型手性固定相的手性自分辨行为。通过使用两种样品制备方法将这些化合物连接到氧化的Si(111)样品和原子力显微镜针尖上,得到了“刷型”手性界面:直接表面沉积和两步表面沉积手性固定相到衬底上。利用原子力显微镜,得到了手性界面的形貌。XPS和FTIR提供了有关化合物在表面上的相对分布的信息。我们用XPS分析了N_1S峰,以确保表面上所有的NH_2基团都被封顶。2-丙醇手性自选择性的化学力光谱测量表明,两个体系都存在手性分辨,但N-(3,5-二硝基苯甲酰基)苯甘氨酸的手性分辨能力更强,这与先前的分子动力学研究结果相一致.
A study of chiral self-discrimination in two model chiral stationary phases, N-(3,5-dinitrobenzoyl-phenylglycine and N-(3,5-dinitrobenzoyl)leucine, is described. “Brush-type” chiral interfaces are obtained by attaching these compounds onto oxidized Si(111) samples and atomic force microscopy tips by using two sample preparation procedures: a direct and a two-step surface deposition of the chiral stationary phase onto the substrate. By using AFM, the morphologies of the resulting chiral interfaces are obtained. XPS and FTIR provide information regarding the relative distribution of the compounds on the surface. We analyze the N 1s peaks using XPS to ensure that all the NH2 groups on the surface are capped. Chemical force spectrometric measurements of the chiral self-selectivity in 2-propanol demonstrate that chiral discrimination is present in both systems, but larger forces are observed for N-(3,5-dinitrobenzoyl)phenylglycine, consistent with a previous molecular dynamics study that demonstrated much weak...