Synthesis, Characterization, Crystal Structure, Hirshfeld Surface, Electronic Excitation, Molecular Docking, and DFT Studies on 2-Amino Thiophene Derivative
Aysha Fatima, Ghazala Khanum, Indresh Verma, Ray J. Butcher, Nazia Siddiqui, Sanjay K. Srivastava, Saleem Javed
Abstract
Ethyl-2-amino-5,6,7,8-tetrahydro-4H-cyclo-hepta[b]thiophene-3-carboxylate (EACHT) has been synthesized, characterized via single-crystal X-ray diffraction at 293 K and investigated quantum chemically by DFT approach, surface analysis by Hirshfeld and spectrochemically by NMR (1H-NMR and 13C-NMR), FTIR, and UV–Visible. The compound crystallizes in monoclinic crystal system with P21/c space group with Z = 4, with following unit cell dimensions: a = 9.5956 (3) Å, b = 9.5607 (4) Å, c = 13.7226 (7) Å. To get the optimized structure which is base for all the other calculations (vibrational frequency, NBO, natural hybrid orbital, nonlinear optical, frontier molecular orbital, etc.), B3LYP method with 6-311++G(d,p) basis set was used. Complete potential energy distribution assignments were done successfully by VEDA. 1H-NMR and 13C-NMR shifts were estimated by GIAO method and results were compared with experimental spectra. TDDFT method and PCM solvent model was utilized for electronic property analysis such as UV–Vis (in gas phase, ethanol, and DMSO) and compared with the experimental UV–Vis spectra. The HOMO and LUMO energy results emphasize adequate charge transfer was happened within the molecule. NBO analysis MEP surface analysis electron localization function Diagram and Fukui function analysis were done. Hole and Electron density distribution maps were drawn in two different excited states of higher oscillatory strength with DMSO, MeOH as solvents. Docking with seven different receptors, and drug likeness was also carried out.