EXPERIMENTAL AND THEORETICAL APPROACHES TO STRUCTURAL, SPECTROSCOPIC, ELECTRONIC, AND NLO PROPERTIES INSECTICIDE CHLORANTRANILIPROLE: MOLECULAR DOCKING AND ADMET ANALYSIS

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Türköz Altuğ D.

BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA, cilt.40, sa.4, ss.735-754, 2026 (SCI-Expanded, Scopus)

Özet

This study aims to investigate the molecular geometry, biological activities, and electronic and

vibrational properties of 5-bromo-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloropyridin-2-

yl)pyrazole-3-carboxamide(Chlorantraniliprole). To support the theoretical results, experimental measurements of

FTIR, Raman, and UV-Vis spectra were performed. Using the DFT/B3LYP/6–311 G(d,p) basis set, the ground

state geometry and electronic structure of chlorantraniliprole were optimized. To predict the chemical reactivity of

the chlorantraniliprole molecule, molecular electrostatic potential (MEP) maps, frontier molecular orbital (FMO)

analysis, and electronic reactivity descriptors were employed. The energies of the highest occupied molecular orbital

(HOMO) and lowest unoccupied molecular orbital (LUMO) were examined to elucidate the intramolecular charge

transfer characteristics. Natural bond orbital (NBO) analysis was conducted to evaluate the electronic characteristics

and stabilization energies of intra- and intermolecular hydrogen bonding interactions. Molecular docking studies

were performed with human DNA (1BNA) and tumor suppressor protein p53 (2ACO) to explore potential off-target

interactions of chlorantraniliprole. The best binding affinities, based on the results, were determined to be -7.1 and

-6.7 kcal/mol, respectively. The compound chlorantraniliprole demonstrates an unfavorable pharmacokinetic profile

for human health, based on drug likeness, physicochemical properties, and ADMET data.