Synthesis, molecular docking of 3-(2-chloroethyl)-2,6-diphenylpiperidin-4-one: Hirshfeld surface, spectroscopic and DFT based analyses

• Published in: Journal of molecular structure 2022-08, Vol.1262, p.132993, Article 132993
• Main Authors: Kumar, Anitha, Sambandam, Sivakumar, Ramalingam, Arulraj, Krishnamoorthy, Rajkumar, Arumugam, Dhandapani, Oyeneyin, Oluwatoba Emmanuel
• Format: Article
• Language: English
• Subjects: DFT; Hirshfeld surface analysis; HOMO-LUMO; Molecular docking; Vibrational Spectra
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2022.132993

•The title compound CEDP were characterized by FT-IR, NMR, XRD, FT-Raman and UV-Visible spectrum.•NBO, MEP and NLO were investigated by DFT/B3LYP/6–311++G(d,p).•UV–Visible spectrum, HOMO-LUMO and Hirshfeld surface discussed.•Anti-influenza potential was investigated via Molecular docking. In this work, 3-(2-chloroethyl)-2,6-diphenylpiperidin-4-one (CEDP) was synthesized, characterized via spectroscopic techniques (FT-IR, FT-Raman, UV–Vis, 1H and 13C NMR) and optimized using the Density Functional Theory (DFT) approach with a hybrid correlation, B3LYP/6–311++G(d,p) level of theory. The molecular electrostatic potential (MEP) and natural bond orbitals (NBO) were calculated. The molecule was also docked at the active sites of Influenza A virus receptors. The NBO results revealed the occurrence of hyperconjugation and delocalization of π-electrons. Hirshfeld surface and fingerprint analysis were used to examine the intermolecular hydrogen bonding and electron density of the crystal structure. The inter contact forces are C···H/H···C (19.9%), O···H/H···O (8.0%), Cl···H/H···Cl (11.8%), H···H (58.7%) and N···H/H···N (0.8%). The energy gap of CEDP was found to be 5.42 eV, suggesting its stability. Extra precision docking results revealed that CEDP binds well with both RNA polymerase PB1-PB2 and neuraminidase receptors, with similar interactions observed as compared with the standard drugs. [Display omitted]