文献类型：期刊文献

英文题名：Resolution Characteristics of Optically Active (1S,2S)-(+)-1-(p-Nitrophenyl)-2-Amino-1,3-Propanediol for trans-1,2-Cyclohexanedicarboxylic Acid

作者：Jin, Haibing[1];Peng, Yangfeng[1];Tong, Tianzhong[1];Zhao, Hongliang[1];Dai, Yani[1];He, Quan[2]

机构：[1]East China Univ Sci & Technol, Sch Chem Engn, Shanghai, Peoples R China;[2]Dalhousie Univ, Fac Agr, Dept Engn, Truro, NS, Canada

年份：2025

卷号：37

期号：12

外文期刊名：CHIRALITY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:001630387600001)】；

语种：英文

外文关键词：chiral resolution; crystal structure; energy frameworks; formation of conglomerate salts; Hirshfeld surface; trans-1,2-cyclohexanedicarboxylic acid

摘要：The resolution behavior of chiral compounds containing two carboxyl groups remains an interesting subject due to their potential for forming complex stereospecific interactions. In this study, a representative for this group of compounds, trans-1,2-cyclohexanedicarboxylic acid (CHDA) was enantiomerically separated using optically active (1S,2S)-(+)-1-(p-nitrophenyl)-2-amino-1,3-propanediol ((SS)-ANP) as a resolving agent in ethanol solvent. Remarkably, regardless of the initial molar ratio of (SS)-ANP to CHDA (ranging from 1:3 to 3:1), only a cocrystal, di-(SS)-ANPCHDAethanol was obtained. When the molar ratio was adjusted to 1:2, a pair of diastereomeric salts was formed, and (RR)-CHDA freed from the less soluble diastereomeric salt exhibited an enantiomeric excess (e.e.) exceeding 85%. Upon two cycles of recrystallization of the less soluble salts, the optical purity of the freed (RR)-CHDA reached 96.5 e.e.%. To elucidate the resolution mechanism, single crystals of both the less soluble salt 2(SS)-ANP(RR)-CHDAethanol and the more soluble salt 2(RR)-ANP(RR)-CHDAethanol were grown and structurally analyzed. The crystallographic data revealed that the hydrogen bonding in the less soluble salt was stronger than that in the more soluble salt, enhancing the stability of the less soluble salt, 2(SS)-ANP(RR)-CHDAethanol.