Synthesis, crystal structure, antibacterial activities, and electrochemical studies of new N,N′-polymethylene bis-sulfonamides

Four disulfonamide derivatives (C2H5·SO2·NH)2(CH2)n (n = 2, 3, 4, 5) were synthesized and characterized by FTIR, 1H NMR, 13C NMR, HETCOR, LCMS and elemental analysis. Ethanesulfonamide-N,N′-pentamethylene bis was also characterized by X-ray single crystal diffraction measurement. The electrochemical characteristics of the disulfonamide derivatives were performed by cyclic voltammetry and chronoamperometry. 1H and 13C NMR chemical shifts of the compounds were calculated by using DFT/B3LYP methods with a 6-311++G (d,p) basis set. Antibacterial activity and the structural relationship of the compounds showed that activity decreases proportionately to the increasing length of the carbon chain between NH groups, log P values, hydration energy and molecular volumes. Anodic peak potentials and HOMO values do not correlate with the activity, but reduction potential and LUMO decrease weakly with increasing activity.

► Synthesis and characterization of disulfonamide derivatives (C2H5·SO2·NH)2(CH2)n (n = 2, 3, 4, 5).
► Antimicrobial activities disulfonamide derivatives.
► The electrochemical characteristics of the disulfonamide derivatives.