文献类型：期刊文献

英文题名：Resolution of 2-chloromandelic acid with (R)-(+)-N-benzyl-1-phenylethylamine: chiral discrimination mechanism

作者：Peng, Yangfeng[2];He, Quan[1];Rohani, Sohrab[1];Jenkins, Hilary[3]

机构：[1]Univ Western Ontario, Dept Chem & Biochem Engn, London, ON N6G 4R3, Canada;[2]E China Univ Sci & Technol, Dept Chem Engn, Shanghai 200237, Peoples R China;[3]McMaster Univ, Dept Chem & Chem Biol, Hamilton, ON, Canada

年份：2012

卷号：24

期号：5

起止页码：349

外文期刊名：CHIRALITY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000303237200001)】；

语种：英文

外文关键词：2-chloromandelic acid; (R)-(+)-N-benzyl-1-phenylethylamine; crystallization resolution; diastereomeric salt; chiral discrimination; chiral recognition; hydrogen bond; CH; p interaction; van der Waals

摘要：During the resolution of 2-chloromandelic acid with (R)-(+)-N-benzyl-1-phenylethylamine, the crystals of the less soluble salt were grown, and their structure were determined and presented. The chiral discrimination mechanism was investigated by examining the weak intermolecular interactions (such as hydrogen bond, CH/p, and van der Waals interactions) and molecular packing mode in crystal structure of the less soluble diastereomeric salt. A one-dimensional double-chain hydrogen-bonding network and a lock-and-key supramolecular packing mode are disclosed. The investigation demonstrates that hydrophobic layers with corrugated surfaces can fit into the grooves of one another to realize a compact packing, when the molecular structure of resolving agent is much larger than that of the racemate. This lock-and-key assembly is recognized to be another characteristic of molecular packing contributing to the chiral discrimination, in addition to the well-known sandwich-like packing by hydrophobic layers with planar boundary surfaces. Chirality 24:349355, 2012. (c) 2012 Wiley Periodicals, Inc.