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Salt‐Solubilization and Ion‐Pair Recognition by a Quinoline‐Substituted Crown Ether
Author(s) -
Sun ZhanHu,
Pan FangFang,
Albrecht Markus,
Raabe Gerhard
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301032
Subject(s) - chemistry , quinoline , crown ether , salt (chemistry) , moiety , halide , ether , solubilization , inorganic chemistry , ion , solvent , medicinal chemistry , organic chemistry , polymer chemistry , biochemistry
Abstract A novel quinoline‐substituted crown ether has been synthesized as a receptor for ion pairs and its binding behavior was investigated in various solvents. The binding of ion pairs in [D 6 ]DMSO and in mixed [D 6 ]DMSO/CD 3 CN/CDCl 3 solvents was studied and the results revealed positive cooperativity effects. As a novel solubilizing agent, the crown ether can extract halide salts into organic media, especially chloride salts. ESI MS provided evidence for the formation of salt‐receptor complexes. A recycling experiment showed that the receptor can solubilize salts and can be recovered. This process can be performed as a cycle. This study validates the idea that a straightforward combination of a common anion receptor and a well‐studied cation complexation moiety enables the formation of ion‐pair receptors and solubilizers of salts in organic solvents.