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Construction of Hydrogen‐Bonded Ternary Organic Crystals Derived from L ‐Tartaric Acid and Their Application to Enantioseparation of Secondary Alcohols
Author(s) -
Kodama Koichi,
Sekine Eriko,
Hirose Takuji
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101839
Subject(s) - tartaric acid , supramolecular chemistry , enantiomer , hydrogen bond , chemistry , molecule , alcohol , diamine , van der waals force , ternary operation , organic chemistry , crystallography , polymer chemistry , computer science , citric acid , programming language
Abstract Ternary organic crystals consisting of an L ‐tartaric acid‐derived dicarboxylic acid, a commercially available achiral diamine, and a chiral secondary alcohol have been developed and characterized by X‐ray crystallography. 1D, 2D, and 3D hydrogen‐bonded supramolecular networks were constructed, depending on the structure of the diamine used. Benzylic and aliphatic secondary alcohols were enantioselectively incorporated into the crystal and were successfully enantioseparated with up to 86 and 79 % enantiomeric excess ( ee ), respectively. Selective incorporation of one enantiomer of 2‐butanol, which is a small chiral aliphatic alcohol, was achieved by the cooperative effects of hydrogen bonds, CH⋅⋅⋅π interactions, and van der Waals interactions between the guest and host molecules, with the aid of two water molecules. The high host potential of the binary supramolecular system is mainly attributed to the skewed conformation of two rigid aromatic groups of tartaric acid derivatives, which prevents dense packing of the molecules and enhances the formation of multicomponent inclusion crystals.