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 ( 1 H, 1 3 C) 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.
Bhardwaj et al. (Thu,) studied this question.