Affiliation:
1. School of Chemical Engineering East China University of Science and Technology Shanghai China
2. Department of Engineering, Faculty of Agriculture Dalhousie University Truro Nova Scotia Canada
Abstract
AbstractTo investigate the thermodynamic and molecular self‐assembly mechanism of trans‐1,2‐cyclohexane dicarboxylic acid containing two carboxylic acid groups in the chiral resolution process, (S)‐phenylethylamine was used as the chiral resolving agent. Two stoichiometric salts were formed when the raw materials were fed at different molar ratios: cyclohexane dicarboxylate monophenylethylamine salt and cyclohexane dicarboxylate diphenylethylamine salt. When the molar ratio of the (S)‐phenylethylamine to trans‐1,2‐cyclohexane dicarboxylic acid was less than 3:1, trans‐(1S,2S)‐cyclohexane dicarboxylic acid was obtained with 97 e.e% purity. But when the molar ratio exceeded 3:1, the product was the racemic trans‐(1,2)‐cyclohexane dicarboxylic acid. In addition, single crystal structures of more soluble mono‐salt, less soluble mono‐salt, and less soluble di‐salt were obtained. The weak intermolecular interactions and the way of the molecules packing in the crystals were analyzed. The hydrogen bond was stronger in the less soluble salt than that in the more soluble salt. And a “lock‐and‐key” structure in the hydrophobic layers makes it more tightly packed through the van der Waals interaction, which is responsible for the stability of less soluble salts.
Funder
National Natural Science Foundation of China
Subject
Organic Chemistry,Spectroscopy,Drug Discovery,Pharmacology,Catalysis,Analytical Chemistry
Cited by
1 articles.
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