p-sulfonatocalix[7]arene:: synthesis, protolysis, and binding ability

被引：29

作者：

Gaeta, Carmine ^{[1
]}

Caruso, Tonino ^{[1
]}

Mincolelli, Milena ^{[1
]}

Troisi, Francesco ^{[1
]}

Vasca, Ermanno ^{[1
]}

Neri, Placido ^{[1
]}

机构：

[1] Univ Salerno, Dipartimento Chim, I-84084 Salerno, Italy

来源：

TETRAHEDRON | 2008年 / 64卷 / 22期

关键词：

calixarenes; calix[7]arenes; water-soluble; molecular recognition; pK(a); spectrofluorimetry;

D O I：

10.1016/j.tet.2008.03.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Water-soluble p-sulfonatocalix[7]arene 1 has been synthesized in good yield through standard procedures and its conformational preferences have been investigated by Monte Carlo conformational searches. The acid-base properties of 1 were investigated by means of potentiometric titration, obtaining pK(a) values in agreement with those reported for other p-sulfonatocalix[n]arene homologs. The binding ability of I toward organic quaternary ammonium cations such as Diquat (2), Paraquat (3), and Chlormequat (4) was investigated by means of H-1 NMR titrations in D2O at pD=7.3, DOSY NMR measurements, and 2D RCESY NMR spectroscopy. Spectrofluorimetry proved to be a useful method for the determination of trace amounts of 2 and 3 in aqueous solution by using Acridine Orange bound to 1 as a chemical indicator. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5370 / 5378

页数：9

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