Electrochemical oxidation of imipramine (IMP) has been studied in aqueous solutions by cyclic voltammetry and controlled-potential coulometry techniques. Our voltammetric results show a complex behavior for oxidation of IMP at different pH values. In this study, we focused our attention on the electrochemical oxidation of IMP at a pH of about 5. Under these conditions, our results show that the oxidation of IMP leads to the formation of a unique dimer of IMP (DIMP). The structure of synthesized dimer is fully characterized by UV–visible, FTIR, 1H NMR, 13C NMR and mass spectrometry techniques. It seems that the first step in the oxidation of IMP is the cleavage of the alkyl group (formation of IMPH). After this, a domino oxidation-hydroxylation-dimerization-oxidation reaction, converts IMPH to (E)-10,10′,11,11′-tetrahydro-[2,2′-bidibenzo[b,f]azepinylidene]-1,1′(5H,5′H)-dione (DIMP). The synthesis of DIMP is performed in an aqueous solution under mild conditions, without the need for any catalyst or oxidant. Based on our electrochemical findings as well as the identification of the final product, a possible reaction mechanism for IMP oxidation has been proposed. Conjugated double bonds in the DIMP structure cause the compound to become colored with sufficient fluorescence activity (excitation wave-length 535 nm and emission wave-length 625 nm). Moreover, DIMP has been evaluated for in vitro antibacterial. The antibacterial tests indicated that DIMP showed good antibacterial performance against all examined gram-positive and gram-negative bacteria (Staphylococcus aureus, Bacillus cereus, Escherichia coli and Shigella sonnei).
This research has led to the development of an environmentally friendly method for the synthesis of some new sulfone derivatives with high yields and without using any toxic reagents and solvents.
Electrochemical synthesis of silver sulfadiazine (AgSD) microcrystals was carried out galvanostatically in a special two-electrode cell equipped with a sacrificial silver rod anode and a stainless steel plate cathode. The cell used in this work consists of a small cylindrical chamber containing aqueous sulfadiazine/sodium nitrate as the anode compartment inside a larger cylindrical chamber containing nitric acid solution as the cathode compartment.The ionic connection of two chambers is carried out through a solvent surface layer. In this study, the effect of the experimental parameters such as applied current density and sodium nitrate concentration as well as nitric acid concentration on the yield and energy consumption of AgSD is discussed. The proposed method is fast and green and has unique features including synthesis in a single step, and no need for a metal salt.
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