Synthesis, single crystal, characterization and computational study of 2-amino-N-cyclopropyl-5-ethyl-thiophene-3-carboxamide

Abstract

2-amino-N-cyclopropyl-5-ethylthiophene-3-carboxamide (ACPETC) (C10H14N2OS) has been synthesized, characterized via single-crystal X-ray diffraction at 296 K and studied theoretically via DFT approach. The compound crystallizes in tetragonal crystal system, space group I-4 with Z = 8 and the following unit cell dimensions: a = 16.0892(4) Å, b = 16.0892(4) Å, c = 8.4059(2) Å. ACPETC was experimentally characterized by 1H, 13C NMR, FT-IR, UV–Vis and ESI-MS analysis. The molecular structure, vibrational spectra, MEP, ELF, NLO, NBO, NHO, and FMO analysis of ACPETC (C10H14N2OS) in the ground state were estimated using HF, MP2, DFT/B3LYP using the 6–311++G(d,p) basis set. Computed NMR chemical shifts (1H and 13C), as well as discrete regions in IR active vibrations, are in good concurrence with their experimental counterparts. FT-IR spectra of ACPETC were obtained in the ranges of 4000−450 cm−1. The UV–vis spectrum as well as the effects of solvents has been studied. The estimated HOMO and LUMO energies reveal that charge transfer happens within the molecule and MEP surface to be a chemically reactive region suitable for drug action. The O1-atom appears to be more vulnerable to electrophilic assault. The NBO analysis was also performed. It indicates that the greatest second order perturbation energy E(2) = 50.11 kcal/mol associated with electron delocalization from the donor (N15) → π* (C10-O14) acceptor interaction. On the atomic charges of the title chemical, the Fukui function and Mulliken analysis have been calculated. 3-D and 2-D interactions in crystals were studies and Hirshfeld surface analysis was used. To discover the optimum ligand-protein interactions, molecular docking was used using eight protein receptors.