Halogen-Bonding Interaction Stabilizing Cluster-type Diastereomeric Salt Crystals

被引：13
|
作者：
Kobayashi, Yuka [1 ]
Maeda, Jin [1 ]
Ando, Tetsuo [1 ]
Saigo, Kazuhiko [1 ]
机构：
[1] Univ Tokyo, Dept Chem & Biotechnol, Grad Sch Engn, Bunkyo Ku, Tokyo 1138656, Japan
来源：
CRYSTAL GROWTH & DESIGN | 2010年 / 10卷 / 02期
关键词：
CHIRAL RECOGNITION ABILITY; CENTER-DOT-HALOGEN; TOPOCHEMISTRY; CHEMISTRY; PACKING;
D O I：
10.1021/cg9010967
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
O-Ethyl 4-chlorophenylphosphonothioic acid (1) was newly synthesized and applied as it chiral selector for the enantioseparation of racemic 1-(4-halophenyl)ethylamines (halo = F, Cl, Br, I; 2a-d) through diastereomeric salt formation. The phosphonothioic acid I showed an excellent chirality-recognition ability for the fluorinated and iodinated amines 2a and 2d with the dramatic switch of the absolute configuration of the enantio-enriched isomers in the deposited salts from R for the amine 2a to S for the amine 2d. The X-ray crystallographic analyses of the four pairs of diastereomeric salts revealed that halogen-bonding interaction in the salt crystals plays a very important role for the switch.
引用
收藏
页码：685 / 690
页数：6
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