Abstract
The negative peak potential in the CV behavior of (1) by the addition of DNA is attributable to the electrostatic interactions between the compound and DNA, an indicator of the oxidizable behavior of (1) in the presence of negative environment of DNA. [Display omitted]
•Structure of the compound 1 was determined by single crystal X-ray diffraction.•FT-IR and UV–Vis. spectra were recorded and compared with the theoretical results.•The 1H, 13C NMR spectra has also been calculated using GIAO method.•DNA binding and antimicrobial studies have also been performed.•All the theoretical calculations were made using DFT/B3LYP method.
A novel tetra-substituted guanidine, N-isopropyl-N-(4-ferrocenylphenyl)-N′-(2,6-diethylphenyl)-N″-benzoylguanidine (1), [(CH3)2CH)(C5H5FeC5H4C6H4)NC(NHCOC6H5)(NHC6H3(CH2CH3)2] has been synthesized and characterized by elemental analysis, FT-IR, multinuclear (1H, 13C) NMR spectroscopy, single crystal X-rays diffraction analysis and density functional theory based quantum chemical calculations. The torsion angles indicating that the guanidine moiety and carbonyl group are almost co-planar, due to the pseudo hexagonal ring formed by intramolecular NH⋯O hydrogen bonds. The DNA interaction studies performed by cyclic voltammetry and UV–visible spectroscopy are in close agreement with the binding constants (K) 1.4×104 and 1.2×104 respectively. The shift in peak potential, current and absorption maxima of the studied ferrocenyl guanidine in the presence of DNA discovered that CV coupled with UV–vis spectroscopy could provide an opportunity to elaborate DNA interaction mechanism, a prerequisite for the design of new drug like agents and understanding the molecular basis of their action. The synthesized compound (1) has also been screened for their antibacterial and antifungal.