Quantum chemical, experimental, theoretical spectral (FT-IR and NMR) studies and molecular docking investigation of 4,8,9,10-tetraaryl-1,3-diazaadamantan-6-ones

The compounds 4,8,9,10-tetraaryl-1,3-diazaadamantan-6-ones ( a – e) were synthesized and characterized by FT-IR, 1 H and 13 C NMR spectra, and the spectral data have been theoretically analyzed by the DFT method. The electronic properties including a highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO) and related parameters were calculated with B3LYP/6-311 G (d, p) basis set. The observed HOMO and LUMO mappings describe the different charge transfer possibilities within the molecule. Besides, the reactive properties of the molecules have been addressed based on the frontier molecular orbital analysis. The Molecular Electrostatic Potential and Fukui function analysis reveal the sites for electrophilic attack and nucleophilic reactions in the molecule. The intramolecular contacts have been interpreted using Natural Bond Orbital analysis and the thermodynamic properties also presented. The molecular docking study has been executed to study the binding interactions of the synthesized compounds with H1N1 swine virus-M2 proton channel and COX-2 protein. Graphical abstract