Fungicide compound 2, 3-dichloronaphthalene-1, 4-dione: Non-covalent interactions (QTAIM, RDG and ELF), combined vibrational spectroscopic investigations using DFT approach with experimental analysis, electronic, molecular docking scrutiny in-vitro assay and thermodynamic property analysis

Abstract

• The observed bond angle distortion of the naphthalene ring, typically between 0.1° and 0.2°, provides evidence of this deviation's magnitude. • The ELF values around hydrogen and chlorine atoms suggest a higher degree of electron localization between bonding and non-bonding electron zones. • The RDG isosurface reveals that the red regions are concentrated within an aromatic naphthalene ring, indicating steric repulsions. • Drug likeness assesses the potential activity of a drug using Lipinski's rule. Structural features and intramolecular interactions have been investigated with quantum mechanical calculations using DFT at the B3LYP level using a 6-311G(d,p) basis set. The study employed several spectroscopic techniques, such as FT-IR, FT-Raman, and UV–Vis, to investigate the molecular structure of 2,3-dichloronaphthalene-1,4-dione (DCND). An energy of 14.82 kJ/mol is required to stabilize the connection between the LP(Cl 13 ) and the antibonding C 8 -C 7 , which suggests significant delocalization. The TDM analysis reveals plots demonstrating the ability to transmit charges. In ALIE analysis blue is employed to depict the stable sigma bonds, which tend to be tied to hydrogen atoms that generate protons. Achieving drug-likeness and ADMET assessment allowed for the biological characteristics of DCND to be evaluated. For docking analysis, the most potent inhibitor, 4YNU, is particularly remarkable since it can form up to five C–H–O hydrogen bonds yielding a binding energy of −6.4 kcal/mol.