In this study, a series of chiral stationary phases based on N ‐[(4‐methylphenyl)sulfonyl]‐l ‐leucine amide, whose enantiorecognition property has never been studied, were synthesized. Their enantioseparation abilities were chromatographically evaluated by 67 enantiomers. The chiral stationary phase derived from N ‐[(4‐methylphenyl)sulfonyl]‐l ‐leucine showed much better enantioselectivities than that based on N ‐(4‐methylbenzoyl)‐l ‐leucine amide. The construction of C ₂ symmetric chiral structure greatly improved the enantiorecognition performance of the stationary phase. The C ₂ symmetric chiral stationary phase exhibited superior enantioresolutions to other chiral stationary phases for most of the chiral analytes, especially for the chiral analytes with C ₂ symmetric structures. By comparing the enantioseparations of the enantiomers with similar structures, the importance of hydrogen bond interaction, π–π interaction, and steric hindrance on enantiorecognition was elucidated. The enantiorecognition mechanism of trans ‐N ,N ′‐(1,2‐diphenyl‐1,2‐ethanediyl)bis‐acetamide, which had an excellent separation factor on the C ₂ symmetric chiral stationary phase, was investigated by ¹H‐NMR spectroscopy and 2D ¹H‐¹H nuclear overhauser enhancement spectroscopy.

中文翻译：

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N-[（4-甲基苯基）磺酰基] -1-亮氨酸为手性侧链的新型C2对称手性固定相。

在这项研究中，合成了一系列基于N -[（4-甲基苯基）磺酰基] -1-亮氨酸酰胺的手性固定相，其对映体识别特性从未得到研究。通过67种对映异构体色谱分析了其对映体分离能力。N -[（4-甲基苯基）磺酰基] -1-亮氨酸衍生的手性固定相比基于N-（4-甲基苯甲酰基）-1-亮氨酸酰胺的手性固定相具有更好的对映选择性。的结构c ^ ₂对称手性结构大大提高了固定相的enantiorecognition性能。的Ç ₂对于大多数手性分析物，尤其是具有C ₂对称结构的手性分析物，对称手性固定相表现出优于其他手性固定相的对映体分辨率。通过比较具有相似结构的对映异构体的对映异构体，阐明了氢键相互作用，π-π相互作用和空间位阻对对映体识别的重要性。的enantiorecognition机制反式- Ñ，ñ ' - （1,2-二苯基-1,2-乙二基）双-乙酰胺，其具有在一个极好的分离系数c ^ ₂对称手性固定相，通过研究¹ H-NMR光谱和2D ¹ H‐¹ H核过度疲劳增强光谱。