文献类型：期刊文献

英文题名：Improved Resolution of 4-Chloromandelic Acid and the Effect of Chlorine Interactions Using (R)-(+)-Benzyl-1-Phenylethylamine as a Resolving Agent

作者：Peng, Yangfeng[1];Feng, Cai[1];Rohani, Sohrab[2];He, Quan[3]

机构：[1]East China Univ Sci & Technol, Sch Chem Engn, Shanghai 200237, Peoples R China;[2]Western Univ, Dept Chem & Biochem Engn, London, ON N6A 5B9, Canada;[3]Dalhousie Univ, Fac Agr, Dept Engn, Truro, NS B2N 5E3, Canada

年份：2018

卷号：23

期号：12

外文期刊名：MOLECULES

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000454523000304)】；

基金：This research was funded by the NSERC Discovery grant number [RGPIN 04211].

语种：英文

外文关键词：chlorine interactions; 4-chloromandelic acid; benzyl-1-phenylethylamine; chiral discrimination; resolution

摘要：In order to avoid the disadvantage of commonly used resolving agent 1-phenylethylamine (hereafter: PEA), which is soluble in water, (R)-(+)-benzyl-1-phenylethylamine ((R)-(+)-BPA) was used to resolve 4-chloromandelic acid (4-ClMA) in this study. The optimal resolution conditions were determined: absolute ethanol as a solvent, the molar ratio of 4-ClMA to (R)-(+)-BPA as 1:1, the filtration temperature as 15 degrees C, and the amount of solvent as 1.6 mL/1 mmol 4-ClMA. Thermophysical properties, such as melting point, heat of fusion, and solubility, exhibited significant differences between the less and more soluble salts. The single crystals for the pair of diastereomeric salts were cultivated and their crystal structures were examined thoroughly. In addition to commonly observed interactions like hydrogen bonding and CH/ interactions. The chlorine...chlorine interaction was observed in the less soluble salt presenting as Cl...Cl between adjacent hydrogen network columns, while the Cl/ interaction was observed in the more soluble salt. It was found that halogen interactions played an important role in chiral recognition of 4-ClMA by (R)-(+)-BPA.