ENANTIOMERIC RECOGNITION OF ORGANIC AMMONIUM-SALTS BY CHIRAL PYRIDINO-18-CROWN-6 LIGANDS - A SHORT REVIEW

被引:29
作者
BRADSHAW, JS [1 ]
HUSZTHY, P [1 ]
MCDANIEL, CW [1 ]
OUE, M [1 ]
ZHU, CY [1 ]
IZATT, RM [1 ]
LIFSON, S [1 ]
机构
[1] WEIZMANN INST SCI,DEPT CHEM PHYS,IL-76100 REHOVOT,ISRAEL
关键词
CHIRAL PYRIDINO-18-CROWN-6 LIGANDS; CHIRAL ORGANIC AMMONIUM IONS; ENANTIOMERIC RECOGNITION;
D O I
10.1080/00958979209407947
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A short review of enantiomeric recognition of chiral organic ammonium salts by chiral pyridino-18-crown-6 ligands is presented. Topics include preparation of chiral macrocycles and details of enantiomeric recognition as determined by H-1 NMR and calorimetry techniques. The chiral pyridino-18-crown-6 ligands containing two tert-butyl or two phenyl substituents on chiral macroring carbon atoms exhibited the highest recognition for the enantiomers of [alpha-(1-naphthyl)ethyl]ammonium perchlorate of any chiral pyridino-18-crown-6 ligands studied.
引用
收藏
页码:105 / 114
页数:10
相关论文
共 39 条
[1]   HOST GUEST COMPLEXATION .33. SEARCH FOR NEW CHIRAL HOSTS [J].
ARTZ, SP ;
DEGRANDPRE, MP ;
CRAM, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1486-1496
[2]   TEMPERATURE-DEPENDENT H-1-NMR STUDIES OF THE COMPLEXATION OF SYNTHETIC MACROCYCLIC MULTI-DENTATE COMPOUNDS WITH PRIMARY ALKYLAMMONIUM SALTS - A SHORT REVIEW [J].
BAXTER, SL ;
BRADSHAW, JS .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (02) :233-245
[3]   NEW CONVERSION OF ESTERS TO ETHERS AND ITS APPLICATION TO THE PREPARATION OF FURANO-18-CROWN-6 [J].
BAXTER, SL ;
BRADSHAW, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (04) :831-832
[4]   THE PREPARATION OF NEW CHIRAL DIPHENYL-SUBSTITUTED MACROCYCLIC POLYETHER-DIESTER COMPOUNDS AND THEIR ENANTIOMERIC RECOGNITION OF CHIRAL ORGANIC AMMONIUM-SALTS [J].
BRADSHAW, JS ;
THOMPSON, PK ;
IZATT, RM ;
MORIN, FG ;
GRANT, DM .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (03) :897-901
[5]   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
[6]  
BRADSHAW JS, 1985, J ORG CHEM, V50, P4865
[7]   PREPARATION OF CHIRAL DIPHENYL-SUBSTITUTED POLYETHER-DIESTER COMPOUNDS [J].
BRADSHAW, JS ;
JOLLEY, ST ;
IZATT, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1229-1232
[8]   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
[9]   CATION COMPLEXING PROPERTIES OF SYNTHETIC MACROCYCLIC POLYETHER-DIESTER LIGANDS CONTAINING THE PYRIDINE SUBCYCLIC UNIT [J].
BRADSHAW, JS ;
MAAS, GE ;
LAMB, JD ;
IZATT, RM ;
CHRISTENSEN, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (02) :467-474
[10]   CHIRAL DIAZA-18-CROWN-6 DERIVATIVES [J].
CHADWICK, DJ ;
CLIFFE, IA ;
SUTHERLAND, IO .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (19) :992-994