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<p>The condensation process using an ethanolic solvent was used to generate single crystals of a new Schiff base molecule, 2-Hydroxy-N′-(2-bromobenzylidene)-benzohydrazide (2H2BBH), (2[C<sub>14</sub>H<sub>11</sub>BrN<sub>2</sub>O<sub>2</sub>]), crystallized in the orthorhombic crystal system with the centrosymmetric space group Pna2<sub>1</sub>. The asymmetric unit contains two distinct Schiff base molecules, which are nearly identical to each other. Intermolecular O2—H2<b>···</b>O1 and intramolecular C10—H10<b>···</b>O1 hydrogen bond interactions are among the most common interactions involving the supramolecular cluster in the structure of 2H2BBH. Experimental vibrational spectra (FT-IR and FT-Raman) were analyzed and supported by DFT-B3LYP/6–311 +  + G(d,p) calculations. A strong correlation between the experimental and theoretical bond lengths, angles, and frequencies was observed. Hirshfeld surface analysis quantified dominant intermolecular interactions, notably H···H (33.3%), C···H/H···C (19.2%), and Br···H/H···Br (14.9%) contacts. The UV–Vis absorption spectrum showed a sharp cut-off at 237&#xa0;nm, and the optical band gap was determined to be 4.64&#xa0;eV, which closely matched the theoretical HOMO–LUMO energy gap of 4.7062&#xa0;eV. Additional electronic parameters, including ionization potential (6.4513&#xa0;eV), electron affinity (1.7451&#xa0;eV), electronegativity (4.0982&#xa0;eV), and electrophilicity index (3.5687&#xa0;eV), were also evaluated. The MEP surface revealed potential reactive sites for nucleophilic and electrophilic attack. Fluorescence analysis confirmed violet-blue emissions at 427&#xa0;nm and 490&#xa0;nm, indicating possible application in optoelectronic devices. A molecular docking study with a binding affinity of −&#xa0;7.9&#xa0;kcal/mol has also been obtained to predict the binding interaction against liver cancer protein marker (PDB ID: 5F59). These results establish 2H2BBH as a promising multifunctional compound for future applications in bioactive materials and optoelectronic technologies. </p>

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Synthesis, characterization, and computational study of a benzohydrazide schiff base for electronic and anticancer applications

  • 期刊论文

  • 发表日期：

    2025年6月16日

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  • C. Arunagiri,
  • S. Selvakumar,
  • S. Jeyavijayan,
  • N. Karthik,
  • I. Rama,
  • A. Subashini

摘要

The condensation process using an ethanolic solvent was used to generate single crystals of a new Schiff base molecule, 2-Hydroxy-N′-(2-bromobenzylidene)-benzohydrazide (2H2BBH), (2[C14H11BrN2O2]), crystallized in the orthorhombic crystal system with the centrosymmetric space group Pna21. The asymmetric unit contains two distinct Schiff base molecules, which are nearly identical to each other. Intermolecular O2—H2···O1 and intramolecular C10—H10···O1 hydrogen bond interactions are among the most common interactions involving the supramolecular cluster in the structure of 2H2BBH. Experimental vibrational spectra (FT-IR and FT-Raman) were analyzed and supported by DFT-B3LYP/6–311 +  + G(d,p) calculations. A strong correlation between the experimental and theoretical bond lengths, angles, and frequencies was observed. Hirshfeld surface analysis quantified dominant intermolecular interactions, notably H···H (33.3%), C···H/H···C (19.2%), and Br···H/H···Br (14.9%) contacts. The UV–Vis absorption spectrum showed a sharp cut-off at 237 nm, and the optical band gap was determined to be 4.64 eV, which closely matched the theoretical HOMO–LUMO energy gap of 4.7062 eV. Additional electronic parameters, including ionization potential (6.4513 eV), electron affinity (1.7451 eV), electronegativity (4.0982 eV), and electrophilicity index (3.5687 eV), were also evaluated. The MEP surface revealed potential reactive sites for nucleophilic and electrophilic attack. Fluorescence analysis confirmed violet-blue emissions at 427 nm and 490 nm, indicating possible application in optoelectronic devices. A molecular docking study with a binding affinity of − 7.9 kcal/mol has also been obtained to predict the binding interaction against liver cancer protein marker (PDB ID: 5F59). These results establish 2H2BBH as a promising multifunctional compound for future applications in bioactive materials and optoelectronic technologies.