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A novel C 2 symmetric chiral stationary phase with N ‐[(4‐Methylphenyl)sulfonyl]‐ l ‐leucine as chiral side chains
Author(s) -
Zhu Junchen,
Zhu Lunan,
Wu Yaling,
Cheng Lingping,
Wang Huiying,
Sun Xiaotong,
Shen Jiawei,
Zhou Yang,
Ke Yanxiong
Publication year - 2020
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.202000163
Subject(s) - chemistry , chiral derivatizing agent , sulfonyl , steric effects , enantiomer , amide , chiral column chromatography , hydrogen bond , side chain , stereochemistry , nuclear magnetic resonance spectroscopy , leucine , molecule , organic chemistry , amino acid , alkyl , biochemistry , polymer
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 1 H‐NMR spectroscopy and 2D 1 H‐ 1 H nuclear overhauser enhancement spectroscopy.