期刊
SUPRAMOLECULAR CHEMISTRY
卷 22, 期 11-12, 页码 653-671出版社
TAYLOR & FRANCIS LTD
DOI: 10.1080/10610271003763263
关键词
liquid-liquid anion exchange; anion binding; macrocycle; calixpyrrole; equilibrium model; extraction
资金
- Division of Chemical Sciences, Geosciences and Biosciences, Office Basic Energy Sciences, US Department of Energy
- US Department of Energy [DE-FG02-04ER63741, DE-FG02-01ER15186, DE-FG02-04ER63745]
- National Science Foundation [CHE-0316623]
- University of Malaga (Junta de Andalucia) [P09-TEP-5369]
When certain macrocyclic anion receptors are added to a chloroform solution of the nitrate form of a lipophilic quaternary ammonium salt (methyltri-C8,10-ammonium nitrate, Aliquat 336N), the extraction of sulphate from an aqueous sodium nitrate solution via exchange with the organic-phase nitrate is significantly enhanced. Eight macrocycles were surveyed, including two derivatives of a tetraamide macrocycle, five derivatives of calix[4]pyrrole and -decafluorocalix[5]pyrrole. Under the hypothesis that the enhancement originates from sulphate binding by the anion receptors in the chloroform phase, it was possible to obtain reasonable fits to the sulphate distribution survey data based on the formation of 1:1 and 2:1 receptor:sulphate complexes in the chloroform phase. Apparent 1:1 sulphate-binding constants obtained from the model in this system fell in the range [image omitted]. Comparison of the results for the various anion receptors included in this study reveals that sulphate binding is sensitive to the nature of the substituents on the parent macrocycle scaffolds in a way that does not follow straightforwardly from simple chemical expectations, such as electron-withdrawing effects on hydrogen-bond donor strength.
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