ENANTIOMERIC RECOGNITION OF CHIRAL AMMONIUM-SALTS BY CHIRAL PYRIDINO-18-CROWN-6 AND PYRIMIDINO-18-CROWN-6 LIGANDS - EFFECT OF STRUCTURE AND SOLVENTS

被引：20

作者：

BRADSHAW, JS

HUSZTHY, P

REDD, JT

ZHANG, XX

WANG, TM

HATHAWAY, JK

YOUNG, J

IZATT, RM

机构：

[1] Department of Chemistry, Brigham Young University, Provo

来源：

PURE AND APPLIED CHEMISTRY | 1995年 / 67卷 / 05期

关键词：

D O I：

10.1351/pac199567050691

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral pyridino-18-crown-6 ligands interact with chiral primary organic ammonium salts by hydrogen bonding from the ammonium cation to the pyridino nitrogen and two alternate ring oxygen atoms. Enantiomeric recognition in these interactions are caused by the steric bulk of the substituents at chiral macrocycle ring positions. Recognition is best for the interaction of chiral pyridino-18-crown-6 hosts with the enantiomers of alpha-(1-naphthylethyl)ammonium perchlorate (NapEtHClO(4)) over (alpha-phenylethyl)ammonium perchlorate (PhEtHClO(4)) possibly because of a greater pi-pi overlap between the naphthalene ring of the guest and pyridine ring of the host. Solvents play an important role in the degree of recognition. A binary solvent composed of 7/3 C2H4Cl2/CH3OH (v/v) gave an enhanced degree of recognition. A new chiral pyrimidino-18-crown-6 ligand exhibited recognition for the enantiomers of NapEtHClO(4).

引用

收藏

页码：691 / 695

页数：5

相关论文

共 24 条

[1] THERMOCHEMICAL CYCLE FOR HEAT OF COMPLEXING OF NA+ AND K+ CATIONS WITH CRYPTAND-222 IN WATER AND METHANOL [J].

ABRAHAM, MH ;

NAMOR, AFDD ;

LEE, WH .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (23) :893-894

[2] ENANTIOMERIC RECOGNITION OF ORGANIC AMMONIUM-SALTS BY CHIRAL PYRIDINO-18-CROWN-6 LIGANDS - A SHORT REVIEW [J].

BRADSHAW, JS ;

HUSZTHY, P ;

MCDANIEL, CW ;

OUE, M ;

ZHU, CY ;

IZATT, RM ;

LIFSON, S .

JOURNAL OF COORDINATION CHEMISTRY, 1992, 27 (1-3) :105-114

[3] 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

[4] CHIRAL DIAZA-18-CROWN-6 DERIVATIVES [J].

CHADWICK, DJ ;

CLIFFE, IA ;

SUTHERLAND, IO .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (19) :992-994

[5] CHIRAL HOST-GUEST RECOGNITION IN AN ION-MOLECULE REACTION [J].

CHU, IH ;

DEARDEN, DV ;

BRADSHAW, JS ;

HUSZTHY, P ;

IZATT, RM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4318-4320

[6] THE DESIGN OF MOLECULAR HOSTS, GUESTS, AND THEIR COMPLEXES [J].

CRAM, DJ .

SCIENCE, 1988, 240 (4853) :760-767

[7] 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

[8] PRACTICAL SYNTHESIS OF A HIGHLY ENANTIOSELECTIVE RECEPTOR FOR PEPTIDES [J].

ERICKSON, SD ;

SIMON, JA ;

STILL, WC .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) :1305-1308

[9] CHEMISTRY OF 2-SUBSTITUTED PYRIMIDINES - STUDIES DIRECTED TOWARD THE SYNTHESIS OF THE PYRIMIDINE MOIETY OF BLEOMYCIN [J].

HAGMANN, WK ;

BASHA, FZ ;

HASHIMOTO, M ;

FRYE, RB ;

KOJO, S ;

HECHT, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (07) :1413-1423

[10] EFFECT OF LIGAND SOLVATION ON STABILITY OF METAL-COMPLEXES IN SOLUTION - EXPLANATION OF MACROCYCLIC EFFECT [J].

HINZ, FP ;

MARGERUM, DW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (15) :4993-4994