Computational study on the Structural and Spectroscopic Properties, Solvent Effects, Topological Insights, and Biological Activities of 2-[1-(2, 4-dichlorobenzyl)-1H-indazol-3-yl] Propan-2-ol as an Anticonvulsant Drug
DOI:
https://doi.org/10.54392/irjmt25215Keywords:
DFT, Solvent Effect, NBO, Chemical Shifts, MEP, Molecular DockingAbstract
In this study, computational methods were employed to investigate the structural, vibrational, chemical shift, topological, thermodynamical, and biological properties of 2-[1-(2,4-dichlorobenzyl)-1H-indazol-3-yl]propan-2-ol (DCBIP), along with solvent effects on its electronic spectra, frontier molecular orbitals (FMO), and molecular electrostatic potential (MEP) surfaces. Molecular geometry analysis identified seven bond types and nine bond angles. Vibrational analysis confirmed 108 fundamental modes associated with OH, CO, CH, CC, CN, NN, CCl, CH₂, and CH₃ functional groups. Chemical shift analysis validated the structural integrity of DCBIP, with deshielding effects observed for key carbons and protons due to electronegative interactions, hydrogen bonding, and inductive effects from chlorine substituents. The consistent FMO energy gap (4.9797–4.9879 eV) across solvents suggests minimal solvent influence, with greater stability in polar environments. Natural bond orbital (NBO) analysis identified the strongest stabilization from the lone pair (LP) of N4 donating to the antibonding σ*(C8-C9) orbital (40.25 kJ/mol), enhancing delocalization in the indazole ring. Mulliken analysis revealed O3 as the most electronegative site and C9 as the most electropositive, while MEP maps confirmed nucleophilic regions over O3 and electrophilic sites over aromatic hydrogens. The specific heat capacity of DCBIP (77.31 cal mol⁻¹K⁻¹) reflects its moderate thermal energy absorption, influenced by vibrational contributions from its complex structure. Topological analyses highlighted electron localization at hydrogen atoms (H32, H37), delocalization in six-membered rings, and the presence of van der Waals interactions and steric effects in DCBIP. Molecular docking studies of DCBIP with 1EOU and 5FDC demonstrated strong binding affinities of -6.89 kcal/mol and -7.45 kcal/mol, respectively, suggesting its potential as an anticonvulsant agent.
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