MOLECULAR RECOGNITION OF ALKYLAMINES - CONFORMATIONAL AND BINDING-PROPERTIES OF CALIX[6]ARENE-BASED ESTER LIGANDS

被引：37

作者：

HAN, SY ^{[1
]}

KANG, MH ^{[1
]}

JUNG, YE ^{[1
]}

CHANG, SK ^{[1
]}

机构：

[1] CHUNG ANG UNIV,DEPT CHEM,SEOUL 156756,SOUTH KOREA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1994年 / 04期

关键词：

D O I：

10.1039/p29940000835

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of alkyl 1(5),3(5),5(5),7(5),9(5),11(5)-hexa-tert-butyl-1,3,5,7,9,11-hexa[1,3]benzenacyclododecaphane esters have been prepared that selectively bind to alkylammonium cations. Ester ligands showed extraction efficiency toward alkylamines in the sequence of ammonium < Me similar or equal to Pt > Pr > Pr-i > Bu > Bu(i) similar or equal to Bu(5) > tert-butylammonium guests. Single and competitive transport experiments of butylamines also confirmed the binding properties obtained with extraction experiments and the transport selectivity for Bu/Bu(t) pair exceeds 25. Conformational properties, such as T-c and Delta G(c)(double dagger) , of ester ligands were investigated by means of temperature-dependent H-1 NMR spectroscopy. Conformational freedom was generally found to decrease as the size of substituent of ester side chain increased. H-1 NMR complexation studies of ethyl ester 2 with caesium tetraphenylborate and butylammonium picrate guests suggest that the conformational reorganization into a cone conformation has provoked complex formation.

引用

页码：835 / 839

页数：5

共 38 条

[1] PERHYDROTRIQUINACENIC HOSTS .2. SYNTHESIS AND COMPLEXATION PROPERTIES OF SPELEANDS OF C3 SYMMETRY [J].