SELECTIVE RECOGNITION OF CARBOXYLATE ANIONS BY POLYAMMONIUM RECEPTORS IN AQUEOUS-SOLUTION - CRITERIA FOR SELECTIVITY IN MOLECULAR RECOGNITION

被引:70
作者
BENCINI, A
BIANCHI, A
BURGUETE, MI
DAPPORTO, P
DOMENECH, A
GARCIAESPANA, E
LUIS, SV
PAOLI, P
RAMIREZ, JA
机构
[1] UNIV FLORENCE,DEPT CHEM,I-50144 FLORENCE,ITALY
[2] UNIV JAUME 1,DEPT EXPTL SCI,ORGAN CHEM LAB,E-12080 CASTELLO DE PLANA,SPAIN
[3] UNIV FLORENCE,DEPT ENERGET,FLORENCE,ITALY
[4] UNIV VALENCIA,DEPT INORGAN CHEM,E-46100 BURJASSOT,SPAIN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1994年 / 03期
关键词
D O I
10.1039/p29940000569
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The interaction in aqueous solution of the polyammonium receptor 1,4,7,10.13,16,19-heptaazacyclohenicosane (8, [21]aneN(7)) with the carboxylic species, 1,2- benzenedicarboxylic (1), 1.3-benzenedicarboxylic (2), 1.2,3-benzenetricarboxylic (3), 1,3,5-benzenetricarboxylic (4), cis,cis-1,3,5-trimethyl-1,3,5-cyclohexanetricarboxylic (5), cis,trans-1.3.5-trimethyl-1,3.5-cyclohexanetricarboxylic (6). and citric (7) acids has been followed by potentiometry and cyclic voltammetry at 298.1 K in 0.15 mol dm(-3) NaClO4, as well as by NMR spectroscopy. The analysis of the potentiometric and electrochemical data show the formation of 1:1 adducts. A novel method based on both potentiometry and cyclic voltammetry to establish selectivity patterns in systems presenting different protonation possibilities is introduced. Preorganization of the substrates in a shape complementary to the receptor yields interesting features such as the selective recognition of 5 over its epimer 6 and recognition of the dicarboxylic species 1 and 2 over the tricarboxylic ones 6 and 7.
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页码:569 / 577
页数:9
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