Synthesis, Crystal Structure Analysis, Quantum Computation, Molecular Docking, and Molecular Dynamics Simulation Studies on 2-(2-phenylazo)-anilino-4,6-di-tert-butyl-phenol

Abstract

The azo-appended o-aminophenol derivative 2-(2-phenylazo)-anilino-4,6-di-tert-butyl-phenol (PABP) was synthesized and comprehensively characterized through experimental and computational methods. Single-crystal X-ray diffraction confirmed its molecular geometry, which showed excellent agreement with DFT-optimized parameters (B3LYP/6-311++G(d,p)). Vibrational (FT-IR) and NMR (1H, 13C) spectra correlated well with theoretical predictions, validating the structural model. TD-DFT calculations in gas and solvent phases elucidated electronic transitions and intramolecular charge-transfer features, supported by HOMO–LUMO analysis and a calculated 3.42 eV band gap. MEP and ELF analyses identified reactive electrophilic and nucleophilic regions and revealed electron-localization characteristics. Hirshfeld surface and fingerprint analyses quantified key intermolecular contacts governing crystal packing. Molecular docking against four CB1 receptor isoforms showed favorable binding affinities and π-driven interactions, further supported by 100-ns MD simulations that confirmed the stability of the best-scoring complex. Overall, the combined structural, spectroscopic and theoretical investigations establish PABP as a stable, electronically versatile molecule with promising potential in materials and bioactive design. © 2026 Wiley-VCH GmbH.