ENANTIOMERIC RECOGNITION OF ORGANIC AMMONIUM-SALTS BY CHIRAL DIALKYL-SUBSTITUTED TRIAZOLE-18-CROWN-6 LIGANDS

被引：40

作者：

LI, Y

ECHEGOYEN, L

MARTINEZDIAZ, MV

DEMENDOZA, J

TORRES, T

机构：

[1] UNIV MIAMI,DEPT CHEM,CORAL GABLES,FL 33124

[2] UNIV AUTONOMA MADRID,DEPT QUIM,E-28049 MADRID,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 13期

关键词：

D O I：

10.1021/jo00013a022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four new chiral triazole-18-crown-6 ligands have been synthesized. The triazole-crowns contain two methyl substituents on the chiral macrocycles, and in the case of 2b and 2c, they also contain lipophilic side arms connected to the triazole ring. Binding constants (K(a)) measured by the H-1 NMR titration technique showed that 2b and 2c exhibited chiral recognition for the enantiomers of [1-(1-naphthyl)ethyl]ammonium cation (HNEA+) and to a lesser extent, for the enantiomers of [1-phenylethyl]ammonium cation (HPEA+). Both S,S chiral hosts recognize preferentially R over S enantiomers.

引用

收藏

页码：4193 / 4196

页数：4

相关论文

共 21 条

[1]

ALONSO JM, 1987, HETEROCYCLES, V26, P989

[2]

[Anonymous], 1996, COMPREHENSIVE SUPERM

[3] PROTON-IONIZABLE CROWN COMPOUNDS .1. SYNTHESIS, COMPLEXATION PROPERTIES, AND STRUCTURAL STUDIES OF MACROCYCLIC POLYETHER DIESTER LIGANDS CONTAINING A TRIAZOLE SUBCYCLIC UNIT [J].

BRADSHAW, JS ;

CHAMBERLIN, DA ;

HARRISON, PE ;

WILSON, BE ;

ARENA, G ;

DALLEY, NK ;

LAMB, JD ;

IZATT, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (17) :3065-3069

[4] PROTON-IONIZABLE CROWN COMPOUNDS .4. NEW MACROCYCLIC POLYETHER LIGANDS CONTAINING A TRIAZOLE SUBCYCLIC UNIT [J].

BRADSHAW, JS ;

NIELSEN, RB ;

TSE, PK ;

ARENA, G ;

WILSON, BE ;

DALLEY, NK ;

LAMB, JD ;

CHRISTENSEN, JJ ;

IZATT, RM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (02) :361-368

[5] PROTON-IONIZABLE CROWN COMPOUNDS .19. THE SYNTHESIS OF CHIRAL DIALKYL-SUBSTITUTED TRIAZOLO-18-CROWN-6 MACROCYCLES [J].

BRADSHAW, JS ;

MCDANIEL, CW ;

KRAKOWIAK, KE ;

IZATT, RM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (05) :1477-1479

[6] ENANTIOMERIC RECOGNITION OF ORGANIC AMMONIUM-SALTS BY CHIRAL DIALKYL-SUBSTITUTED, DIALKENYL-SUBSTITUTED, AND TETRAMETHYL-SUBSTITUTED PYRIDINO-18-CROWN-6 AND TETRAMETHYL-SUBSTITUTED BIS-PYRIDINO-18-CROWN-6 LIGANDS - COMPARISON OF TEMPERATURE-DEPENDENT H-1-NMR AND EMPIRICAL FORCE-FIELD TECHNIQUES [J].

BRADSHAW, JS ;

HUSZTHY, P ;

MCDANIEL, CW ;

ZHU, CY ;

DALLEY, NK ;

IZATT, RM ;

LIFSON, S .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3129-3137

[7]

BRADSHAW JS, 1986, J HETEROCYCLIC CHEM, V26, P353

[8] ENANTIOMERIC RECOGNITION OF ORGANIC AMMONIUM-SALTS BY CHIRAL CROWN ETHERS BASED ON THE PYRIDINO-18-CROWN-6 STRUCTURE [J].

DAVIDSON, RB ;

BRADSHAW, JS ;

JONES, BA ;

DALLEY, NK ;

CHRISTENSEN, JJ ;

IZATT, RM ;

MORIN, FG ;

GRANT, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (02) :353-357

[9] PROTON-IONIZABLE CROWN COMPOUNDS - TRANSPORT OF ALKALI AND ALKALINE-EARTH CATIONS USING PROTON-IONIZABLE TRIAZOLO MACROCYCLES [J].

IZATT, RM ;

LINDH, GC ;

BRADSHAW, JS ;

MCDANIEL, CW ;

BRUENING, RL .

SEPARATION SCIENCE AND TECHNOLOGY, 1988, 23 (12-13) :1813-1823

[10] SEPARATION OF SILVER FROM OTHER METAL-CATIONS USING PYRIDONE AND TRIAZOLE MACROCYCLES IN LIQUID MEMBRANE SYSTEMS [J].

IZATT, RM ;

LINDH, GC ;

BRUENING, RL ;

HUSZTHY, P ;

MCDANIEL, CW ;

BRADSHAW, JS ;

CHRISTENSEN, JJ .

ANALYTICAL CHEMISTRY, 1988, 60 (17) :1694-1699