Synthesis and anion binding studies of a new crown ether containing 2,2′-biimidazole |
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Authors: | Maria C. Llinà s,Joan Farran,Mario V. Capparelli,Gonzalo Anguera,David Sá nchez-Garcí a,Jordi Teixidó ,Salvador Borró s |
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Affiliation: | 1. Grup d’Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, Barcelona 08017, Spain;2. Grup d’Enginyeria dels Materials, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, Barcelona 08017, Spain;3. Enantia, S.L., C/Baldiri Reixac, 10, Barcelona 08028, Spain;4. Unitat de Cristal.lografia, Universitat Autònoma de Barcelona, Bellaterra 08193, Spain |
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Abstract: | 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−. |
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Keywords: | 2,2&prime -Biimidazole Anion binding Crown ether Channels Crystal structure |
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