Experimental spectral characterization, Hirshfeld surface analysis, DFT/TD-DFT calculations and docking studies of (2Z,5Z)-5-(4-nitrobenzylidene)-3-N(2-methoxyphenyl)-2-N’(2-methoxyphenylimino) thiazolidin-4-one

Abstract

We reported an experimental and theoretical spectroscopic studies of (2Z,5Z)-5-(4-nitrobenzylidene)-3-N (2-methoxyphenyl)-2-N’ (2-methoxyphenylimino) thiazolidin-4-one (C24H19N3O5S) molecule, using FT-IR, NMR spectroscopy, and density functional theory (DFT) via time-dependent schema (TD-DFT) respectively. The molecular inter-contacts were explored using Hirshfeld surfaces (HS) analysis method. Vibrational frequencies, gauge-independent atomic orbital (GIAO)1H and13C NMR chemical shift values and frontier molecular orbitals (FMOs) have been calculated from the optimized structure of the molecule by DFT/B3LYP functional with 6-31G(d, p) basis set. Our theoretical results show a good agreement with the experimental data. The calculated UV-visible spectrum employing TD-DFT shows electronic transitions at 388 nm and 495 nm. To get insight on the charge interaction happening inside the molecule, HOMO and LUMO were scrutinized and their calculated energy gap was found to be 2.96 eV. The molecular docking was analyzed via interplay study ofacetyl cholinesterase, and Butyrylcholinesterase using molecular docking methodology.