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

The synthesized (E)-3-(benzofuran-2-yl)-2-(thiophen-2-yl)acrylonitrile (TACNBNF) crystal compound was characterized using FT-IR, H-1 and C-13 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)center dot center dot center dot S (1) donor-acceptor hydrogen bond interaction. The bond angle at C7 gives a strong indication that H7 center dot center dot center dot S1 contact is repulsive. However, the C5-C7-C8 bond angle = 128.8 (2) degrees, 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 H-1 and carbon C-13 NMR chemical shifts of molecules were simulated by the gauge-independent atomic orbital (GIAO) manner and also compared with experimental H-1 and C-13 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. (C) 2019 Elsevier B.V. All rights reserved.