Synthesis and anion binding studies of a new crown ether containing 2,2′-biimidazole

Maria C. Llinàs, Joan Farran, Mario V. Capparelli, Gonzalo Anguera, David Sánchez-García, Jordi Teixidó, Salvador Borrós

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    5 Citations (Scopus)

    Abstract

    © 2014 Elsevier Ltd. A novel crown ether which incorporates the 2,2′-biimidazole moiety was prepared by cyclization of 1,1′-dibenzyl-1H,1′H-[2,2′]biimidazolyl-4,4′-dicarboxylic acid and 4,7,10-trioxa-1,13-tridecanediamine followed by removal of the benzyl groups. The diacid has been obtained by hydrolysis of the diester previously prepared by alcoholysis of the corresponding dicyano biimidazole. The cyano group is introduced by a palladium-catalyzed procedure starting from the corresponding dibromo biimidazole. The macrocyclic structure of the N-dibenzylated derivative of the receptor has been studied by X-ray diffraction. Binding constants for 1:1 biimidazole-anion complexation (Kassoc) are on the order of 105 M-1 for H2PO4- and Cl-.
    Original languageEnglish
    Pages (from-to)4667-4670
    JournalTetrahedron Letters
    Volume55
    Issue number33
    DOIs
    Publication statusPublished - 13 Aug 2014

    Keywords

    • 2,2′-Biimidazole
    • Anion binding
    • Channels
    • Crown ether
    • Crystal structure

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