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

Ahmed Djafri; Fouzia Perveen; Nadia Benhalima; Nawel Khelloul; Rachida Rahmani; Ayada Djafri; Abdelkader Chouaih; Mohammed Benali Kanoun; Souraya Goumri-Said

doi:10.1016/j.heliyon.2020.e05754

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

Heliyon. 2020 Dec 22;6(12):e05754. doi: 10.1016/j.heliyon.2020.e05754. eCollection 2020 Dec.

Authors

Ahmed Djafri^{1

2}, Fouzia Perveen³, Nadia Benhalima^{2

4}, Nawel Khelloul^{2

5}, Rachida Rahmani^{2

6}, Ayada Djafri⁷, Abdelkader Chouaih², Mohammed Benali Kanoun⁸, Souraya Goumri-Said⁹

Affiliations

¹ Centre de Recherche Scientifique et Technique en Analyses Physico-chimiques (CRAPC), BP 384-Bou-Ismail-RP, 42004, Tipaza, Algeria.
² Laboratory of Technology and Solid Properties (LTPS), Abdelhamid IbnBadis University, BP 227, Mostaganem, 27000, Algeria.
³ Research Center for Modeling and Simulations (RCMS), National University of Sciences and Technology, H-12 Campus, Islamabad, Pakistan.
⁴ Département de physique, Faculté des sciences, Université Dr. Moulay Tahar, BP138, EN-NASR, 20000, Saida, Algeria.
⁵ Faculty of Sciences and Technology, Mustapha Stambouli University of Mascara, B.P.763, 29000, Mascara, Algeria.
⁶ Département de Génie des procédés, Centre Universitaire de Relizane, Algeria.
⁷ Laboratoire de Synthèse Organique Appliquées, Faculté des Sciences Exactes et Appliquées, Département de Chimie, Université Oran-1, Algeria.
⁸ Department of Physics, College of Science, King Faisal University, P.O. Box 400, Al-Ahsa, 31982, Saudi Arabia.
⁹ College of Science, Physics Department, Alfaisal University, P.O. Box 50927, Riyadh, 11533, Saudi Arabia.

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.

Keywords: (1H, 13C) NMR; DFT Calculations; Docking; HOMO-LUMO; UV-Visible; X-ray diffraction.