engleski

Mechanochemical synthesis of amide-based supramolecular anion receptors

Traditional synthetic procedures in organic chemistry are generally very successful but global problems of pollution and growing energy demand have compelled the chemical industry to search for new, more efficient and “greener” synthetic methods. Mechanochemical reactions are induced by the direct absorption of mechanical energy and they are mainly promoted by hand grinding or mechanochemical milling. Mechanochemical organic reactions are carried out without the need for solvents or conventional catalysts, and most often feature higher product yield in shorter reaction time. [1] Contrary to the wide knowledge about organic reactions in solution, mechanisms of mechanochemical reactions are still mostly unknown. Only the recently developed in situ monitoring techniques[3] started to unveil the mechanisms of organic mechanochemical reactions, leading to wider application of this methodology in modern material and pharmaceutical industry. [4] Here we present mechanochemical reactions between acyl azide and primary amine as a model nucleophilic substitution reaction on the carbonyl group. We have examined the influence of different additives on reaction time and yields using in situ Raman spectroscopy monitoring and the products were confirmed by 1H and 13C NMR spectroscopy. As amide derivatives are widely investigated as receptors for anions, [5] we studied affinity of the prepared compounds towards biologically important acetate and dihydrogen phosphate anions in solution using 1H NMR spectroscopy.

mechanochemical synthesis ; amide-based ; supramolecular ; anion receptors ; Raman spectroscopy ; in situ monitoring

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