Intramolecular C-H•••O hydrogen bonding reduces cation complexation strength in a fluorescent crown ether

被引：22

作者：

De Wall, SL

Meadows, ES

Barbour, LJ

Gokel, GW

机构：

[1] Washington Univ, Sch Med, Biochem Chem Program, St Louis, MO 63110 USA

[2] Washington Univ, Sch Med, Dept Mol Biol & Pharmacol, St Louis, MO 63110 USA

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 16期

关键词：

D O I：

10.1039/a902676b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Complexes of the fluorescent crown ether, N,N-bis(9-anthrylmethyl)-4,13-diaza-18-crown-6, with NaI3 and KSCN reveal the presence of intramolecular C-H ... O hydrogen bonds that appear to control conformation and lead to reduced cation binding affinity.

引用

收藏

页码：1553 / 1554

页数：2

相关论文

共 18 条

[1] LUMINESCENCE AND CHARGE-TRANSFER .2. AMINOMETHYL ANTHRACENE-DERIVATIVES AS FLUORESCENT PET (PHOTOINDUCED ELECTRON-TRANSFER) SENSORS FOR PROTONS [J].

BISSELL, RA ;

CALLE, E ;

DE SILVA, AP ;

DESILVA, SA ;

GUNARATNE, HQN ;

HABIBJIWAN, JL ;

PEIRIS, SLA ;

RUPASINGHE, RADD ;

SAMARASINGHE, TKSD ;

SANDANAYAKE, KRAS ;

SOUMILLION, JP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (09) :1559-1564

[2]

Czarnik A.W., 1993, ACS S SER, V538

[3] FLUORESCENT SIGNALING CROWN ETHERS - SWITCHING ON OF FLUORESCENCE BY ALKALI-METAL ION RECOGNITION AND BINDING INSITU [J].

DE SILVA, AP ;

DESILVA, SA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (23) :1709-1710

[4] A fluorescent chemosensor for the copper(II) ion [J].

DeSantis, G ;

Fabbrizzi, L ;

Licchelli, M ;

Mangano, C ;

Sacchi, D ;

Sardone, N .

INORGANICA CHIMICA ACTA, 1997, 257 (01) :69-76

[5] The C-H center dot center dot center dot O hydrogen bond: Structural implications and supramolecular design [J].

Desiraju, GR .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (09) :441-449

[6] CROWN CATION COMPLEX EFFECTS .16. SOLVENT DEPENDENCE OF THE 15-CROWN-5 AND 18-CROWN-6 EQUILIBRIA WITH SODIUM-CATION [J].

DISHONG, DM ;

GOKEL, GW .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (01) :147-148

[7] SOLID-STATE STRUCTURAL CHEMISTRY OF LARIAT ETHER AND BIBLE CATION COMPLEXES - METAL-ION IDENTITY AND COORDINATION-NUMBER DETERMINE CAVITY SIZE [J].

GANDOUR, RD ;

FRONCZEK, FR ;

GATTO, VJ ;

MINGANTI, C ;

SCHULTZ, RA ;

WHITE, BD ;

ARNOLD, KA ;

MAZZOCCHI, D ;

MILLER, SR ;

GOKEL, GW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (14) :4078-4088

[8]

GATTO VJ, 1989, ORG SYNTH, V68, P227

[9] LARIAT ETHERS - FROM SIMPLE SIDEARMS TO SUPRAMOLECULAR SYSTEMS [J].

GOKEL, GW .

CHEMICAL SOCIETY REVIEWS, 1992, 21 (01) :39-47

[10]

GOKEL GW, 1990, CATION BINDING MACRO, P253