Synthesis, spectroscopic characterization, crystal structure, DFT insights, NLO properties, and cholinesterase docking studies of a brominated salicylaldehyde Schiff base
Journal of Molecular Structure, cilt.1362, 2026 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 1362
- Basım Tarihi: 2026
- Doi Numarası: 10.1016/j.molstruc.2026.145689
- Dergi Adı: Journal of Molecular Structure
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex, INSPEC, Academic Search Ultimate (EBSCO), Engineering Source (EBSCO)
- Anahtar Kelimeler: ADMET prediction, DFT, Hirshfeld surface analysis, Hyperpolarizability, Molecular docking
- Ondokuz Mayıs Üniversitesi Adresli: Evet
Özet
A new bromine-substituted salicylaldehyde-derived Schiff base, (E)-2,4-dibromo-6-(((3-hydroxy-4-methylphenyl)imino)methyl)phenol, was synthesized and structurally characterized using FT-IR, UV-Vis, and single-crystal X-ray diffraction. The molecule crystallizes in the monoclinic P21/n space group and is stabilized by a strong intramolecular O-H···N hydrogen bond, supporting the enol-imine tautomeric form. DFT calculations (B3LYP/6-31G(d,p)) reproduced the experimental structure with excellent correlation, confirming the reliability of the theoretical model. Hirshfeld surface analysis revealed that H···H, H···Br, and O···H interactions dominate the intermolecular contacts, while energy framework results identified dispersion forces as the primary contributors to crystal packing stabilization. The compound exhibited a substantial first-order hyperpolarizability (β = 87.1 × 10-31esu)) indicates a notable molecular-level nonlinear optical response, although crystal symmetry may limit second-order NLO effects. Molecular docking demonstrated strong binding affinity toward acetylcholinesterase (-9.4 kcal·mol-1) and butyrylcholinesterase (-7.6 kcal·mol-1), supported by hydrophobic and hydrogen-bonding interactions. ADMET predictions indicate generally favorable oral drug-likeness and high gastrointestinal absorption; however, the predicted genotoxic risk highlights the need for further optimization and experimental validation, despite the absence of predicted hepatotoxicity or cardiotoxicity.