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

In this work, 3-(2-chloroethyl)-2,6-diphenylpiperidin-4-one (CEDP) was synthesized, characterized via spectroscopic techniques (FT-IR, FT-Raman, UV-Vis, 1 H and 13 C 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 pi-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 center dot center dot center dot H/H center dot center dot center dot C (19.9%), O center dot center dot center dot H/H center dot center dot center dot O (8.0%), Cl center dot center dot center dot H/H center dot center dot center dot Cl (11.8%), H center dot center dot center dot H (58.7%) and N center dot center dot center dot H/H center dot center dot center dot 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. (c) 2022 Elsevier B.V. All rights reserved.