Synthesis and comparative investigations of DFT/B3LYP, B3PW91, CAM-B3LYP and HSEH1PBE methods applied to molecular structure, spectroscopic analysis, electronic properties of a novel hydrazone having triazole and pyrazole moiety

In this study, we report the synthesis of a novel compound, 4-(((5-(naphthalen-2-yloxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)amino)-5-propyl-4H-1,2,4-triazole-3-thione (7b), which crystallizes in a triclinic system with a $P\bar{1}$ space group. The molecular structure was confirmed by single crystal XRD analysis. To further explore the compound’s properties, we employed density functional theory (DFT) using various functionals such as B3LYP, B3PW91, CAM-B3LYP, and HSEH1PBE with a 6-311G basis set. These computational approaches provided insights into the optimized molecular structure, vibrational frequencies (IR), NMR chemical shifts, frontier molecular orbitals (HOMO-LUMO), molecular electrostatic potential (MEP), and non-covalent interactions. A comparative analysis of the computational methods revealed that B3LYP produced the highest values for vibrational frequencies, NMR chemical shifts, and HOMO-LUMO energy gaps. Molecular docking studies further demonstrated that compound 7b exhibits significant binding affinity with the scores of −6.83 k/cal/mole and −10.58 k/cal/mole for 6LU7 and 7K40 proteins targets respectively against SARS-CoV-2, suggesting its potential antiviral activity. The correlation between experimental data and theoretical predictions supports the reliability of our computational methods and provides a comprehensive understanding of the compound’s structural and electronic properties.