A case of oxoanion recognition based on combined cationic and neutral C–H hydrogen bond interactions. Issue 5 (28th November 2014)

• Record Type: Journal Article
• Authors: Zapata, Fabiola; Sabater, Paula; Caballero, Antonio; Molina, Pedro
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 5(2015)
• Page Start: 1339
• Page End: 1346
• Publication Date: 2014-11-28
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c4ob02288b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A bidentate bis-(benzimidazolium) receptor containing pyrene as fluorescent signaling units recognizes sulphate and hydrogenpyrophosphate in a competitive water–DMSO medium through combinations of cationic and neutral C–H hydrogen bonding. Abstract : A novel bidentate bis-(benzimidazolium) receptor containing pyrene as fluorescent signaling units has been synthesized. Fluorescence and NMR spectroscopy studies reveal that this receptor exclusively recognizes sulphate and hydrogenpyrophosphate in the competitive water–DMSO (1 : 9) medium; significant downfield shifts were observed for the C(2)–H protons of both the imidazolium groups, and appreciable downfield shifts were also observed for the inner naphthalene protons indicating their participation in hydrogen bonding with anions along with the C(2) imidazolium protons. The calculated association constants from 1 H NMR and fluorescence titrations demonstrate that the receptor binds sulphate stronger than hydrogenpyrophosphate anions.