A combined experimental and DFT computations study of novel (E)-3-(benzofuran-2-yl)-2-(thiophen-2-yl)acrylonitrile(TACNBNF): Insight into the synthesis, single crystal XRD, NMR, vibrational spectral analysis, in vitro antioxidant and in silico molecular docking investigation with human peroxiredoxin 5 protein

Abstract The synthesized (E)-3-(benzofuran-2-yl)-2-(thiophen-2-yl)acrylonitrile (TACNBNF) crystal compound was characterized using FT-IR, 1H and 13C NMR analyses, ESI-mass and photoluminescence studies. Single crystal X-ray diffraction investigations reveal that the molecule is associated with the C (7)–H (7) … S (1) donor-acceptor hydrogen bond interaction. The bond angle at C7 gives a strong indication that H7⋯S1 contact is repulsive. However, the C5–C7–C8 bond angle = 128.8 (2) °, is distorted due to strain induced by double bond linkage at C5=C7. The computational work such as optimized geometry by Density functional theory (DFT), FT-IR, Molecular electrostatic potential (MEP), Frontier Molecular orbitals (FMOs), Mulliken's population analysis, Nonlinear optical effects (NLO), and Natural bond orbitals (NBO) were analyzed with the aid of Gaussian 03 program using basic set B3LYP/6–311++G (d,p). The proton 1H and carbon 13C NMR chemical shifts of molecules were simulated by the gauge-independent atomic orbital (GIAO) manner and also compared with experimental 1H and 13C NMR results. The in vitro antioxidant study was carried out in DPPH assay ascorbic acid, a standard drug. The in silico molecular docking, ADMET and toxicity studies were performed by Discovery Studio 4.0.