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Paper | Regular issue | Vol 63, No. 11, 2004, pp.2465-2473
Published online, 17th September, 2004
DOI: 10.3987/COM-04-10139
A Xanthone-based Macrocyclic Receptor and Its Possible Applications

José V. Hernández, Ana I. Oliva, Francisco M. Muñiz, Luis Simón, César Raposo, and Joaquín R. Morán*

*Department of Organic Chemistry, University of Salamanca, Plaza de los Caídos, 1-5, Salamanca, E-37008, Spain

Abstract

A macrocycle (2) based on xanthone units and diphenylethylenediamine is shown to present strong affinity for chloride ion; the extraction of sodium chloride from water to chloroform is possible in the presence of (2) and 18-crown-6 ether. Carboxylates also show strong affinities for (2) in MeOH, but no significant chiral recognition was detected for either naproxenate or ibuprofenate. Zwitterionic amino acids are also extracted from water to chloroform in the presence of 18-crown-6 ether. A modest degree of chiral discrimination was observed for phenylalanine, phenylglycine and t-leucine.