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Aromatic mono- and bis-amide derivatives as anion receptors in solution

Chemistry of anion recognition and complexation has developed into an important field of supramolecular chemistry, with ever-new application potentials of the corresponding systems discovered [1]. Despite a significant progress in the field, the search for receptors exhibiting peak selectivity and high binding affinity continues [2]. In order to facilitate the design of efficient anion ligands, it is of great importance to identify the interactions that lead to the complex formation and assess their individual contribution to the overall stability [3]. One of the feasible approaches towards this goal is to study series of relatively simple model compounds, gaining detailed insight into the interplay of their structure and reactivity [4]. Thus gathered knowledge can be employed in the systematic development of the novel anion receptors as it can point out the suitable type and number of the binding moieties as well as the appropriate linkers to achieve the desired properties. In this work we present the synthesis and the anion complexation study of a series of amide derivatives differing in number and arrangement of the binding sites (amide N–H groups). The stability of their complexes with acetate, dihydrogen phosphate, and chloride was studied in dimethyl sulfoxide using 1H NMR spectroscopy and conductometry. The stoichiometry of all complexes was found to be 1:1 and their stability was discussed with respect to the receptor structural properties as well as specific features of the anions.

anion binding ; amide derivatives ; thermodynamics ; stability constant ; solvation

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