UREA-DERIVATIZED P-TERT-BUTYLCALIX[4]ARENES - NEUTRAL LIGANDS FOR SELECTIVE ANION COMPLEXATION

被引：206

作者：

SCHEERDER, J ^{[1
]}

FOCHI, M ^{[1
]}

ENGBERSEN, JFJ ^{[1
]}

REINHOUDT, DN ^{[1
]}

机构：

[1] UNIV TWENTE,ORGAN CHEM LAB,7500 AE ENSCHEDE,NETHERLANDS

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 25期

关键词：

D O I：

10.1021/jo00104a044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Functionalization of the lower rim of p-tert-butylcalix[4]arene with four (thio)urea groups, results in a class of receptors selective for spherical onions that-are bound exclusively through hydrogen bonding. H-1 NMR spectroscopy in CDCl3 reveals a selectivity for Cl- over Br- and I-. The stoichiometry is 1:1 in all cases as was confirmed by Job plots. The association constants are strongly dependent on the nature of the substituent at the urea moiety. The bidentate phenylurea derivative 9 shows the strongest complexation (K-ass. Cl- = 7.1 x 10(3) M(-1)) and the largest selectivity for Cl-.

引用

页码：7815 / 7820

页数：6

共 60 条

[1] SYNTHETIC ANALOGS OF THE RISTOCETIN BINDING-SITE - NEUTRAL, MULTIDENTATE RECEPTORS FOR CARBOXYLATE RECOGNITION [J].

ALBERT, JS ;

HAMILTON, AD .

TETRAHEDRON LETTERS, 1993, 34 (46) :7363-7366

[2] NEW CLASSES OF ANION RECEPTOR-CONTAINING CHARGED AND NEUTRAL TRANSITION-METAL LEWIS ACIDIC RECOGNITION SITES [J].

BEER, PD ;

DICKSON, CAP ;

FLETCHER, N ;

GOULDEN, AJ ;

GRIEVE, A ;

HODACOVA, J ;

WEAR, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (10) :828-830

[3] ANION RECOGNITION BY ACYCLIC REDOX-RESPONSIVE AMIDE-LINKED COBALTOCENIUM RECEPTORS [J].

BEER, PD ;

HAZLEWOOD, C ;

HESEK, D ;

HODACOVA, J ;

STOKES, SE .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (08) :1327-1332

[4] ACYCLIC REDOX RESPONSIVE ANION RECEPTORS CONTAINING AMIDE LINKED COBALTICINIUM MOIETIES [J].

BEER, PD ;

HESEK, D ;

HODACOVA, J ;

STOKES, SE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (03) :270-272

[5] DICARBOXYLATE ANION RECOGNITION BY A REDOX-RESPONSIVE DITOPIC BIS(COBALTICINIUM) CALIX[4]ARENE RECEPTOR MOLECULE [J].

BEER, PD ;

DREW, MGB ;

HAZLEWOOD, C ;

HESEK, D ;

HODACOVA, J ;

STOKES, SE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (03) :229-231

[6] MACROCYCLES CONTAINING TIN - PREPARATION OF MACROBICYCLIC LEWIS ACIDIC HOSTS CONTAINING 2 TIN ATOMS AND SN-119 NMR-STUDIES OF THEIR CHLORIDE AND BROMIDE BINDING-PROPERTIES IN SOLUTION [J].

BLANDA, MT ;

HORNER, JH ;

NEWCOMB, M .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (19) :4626-4636

[7] THE RELATIVE EASE OF REMOVING A PROTON, A HYDROGEN-ATOM, OR AN ELECTRON FROM CARBOXAMIDES VERSUS THIOCARBOXAMIDES [J].

BORDWELL, FG ;

ALGRIM, DJ ;

HARRELSON, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5903-5904

[8] CHEMICALLY MODIFIED FIELD-EFFECT TRANSISTORS - A SODIUM-ION SELECTIVE SENSOR BASED ON CALIX[4]ARENE RECEPTOR MOLECULES [J].

BRUNINK, JAJ ;

HAAK, JR ;

BOMER, JG ;

REINHOUDT, DN ;

MCKERVEY, MA ;

HARRIS, SJ .

ANALYTICA CHIMICA ACTA, 1991, 254 (1-2) :75-80

[9] TRANSDUCTION OF SELECTIVE RECOGNITION BY PREORGANIZED IONOPHORES - K+ SELECTIVITY OF THE DIFFERENT 1,3-DIETHOXYCALIX[4]ARENE CROWN-ETHER CONFORMERS [J].

BRZOZKA, Z ;

LAMMERINK, B ;

REINHOUDT, DN ;

GHIDINI, E ;

UNGARO, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (06) :1037-1040

[10] NEW METAL CATION-SELECTIVE IONOPHORES DERIVED FROM CALIXARENES - THEIR SYNTHESES AND ION-BINDING PROPERTIES [J].

CHANG, SK ;

CHO, I .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (02) :211-214

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