Enantiomeric recognition of α-(1-naphthyl)ethylammonium perchlorate by enantiomerically pure dimethylphenazino-18-crown-6 ligand in solid and gas phases

被引：16

作者：

Gérczei, T

Böcskei, Z

Keseru, GM

Samu, E

Huszthy, P ^{[1
]}

机构：

[1] Hungarian Acad Sci, Res Grp Alkaloid Chem, H-1521 Budapest, Hungary

[2] Eotvos Lorand Univ, Dept Theoret Chem, H-1521 Budapest, Hungary

[3] Tech Univ Budapest, Dept Chem Informat Technol, H-1521 Budapest, Hungary

[4] Tech Univ Budapest, Inst Organ Chem, H-1521 Budapest, Hungary

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 10期

基金：

匈牙利科学研究基金会;

关键词：

D O I：

10.1016/S0957-4166(99)00208-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

X-Ray crystallographic studies of enantiomerically pure dimethylphenazino-18-crown-6 ligand (R,R)-1 and its complexes with the enantiomers of alpha-(1-naphthyl)ethylammonium perchlorate NapEt were carried out. These studies clearly show that the heterochiral complex (R,R)-1-(S)-NapEt is more stable than the homochiral one (R,R)-1-(R)-NapEt. It was pointed out that besides the hydrogen bonding, mainly the pi-pi interaction between the aromatic systems of the host and guest, and the difference in steric repulsions were responsible for enantioselectivity. Molecular mechanical calculations using the LMOD/MINTA method also predicted the heterochiral complex to be more stable than the homochiral one in the gas phase. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1995 / 2005

页数：11

共 22 条

[1]

[Anonymous], 1994, SPARTAN

[2] Conformational analysis of (S,S)-dimethyl-diketopyridino-18-crown-6 [J].