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

Abstract

Four disulfonamide derivatives (C2H5 center dot SO2 center dot NH)(2)(CH2)(n) (n = 2, 3, 4, 5) were synthesized and characterized by FTIR, H-1 NMR, C-13 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. H-1 and C-13 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. (C) 2011 Elsevier B.V. All rights reserved.