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<p>Vanillin sulfonate derivatives are an important class of functional organic compounds with promising applications in materials science and molecular design. In this study, vanillin sulfonate derivatives <b>(1–9)</b> bearing halogen (F, Cl, Br), nitro (NO<sub>2</sub>), and methoxy (OCH<sub>3</sub>) substituents were investigated using a combined experimental and computational approach. Density functional theory calculations were performed at the B3LYP/6-31G(d, p) level to evaluate their structural stability, electronic properties, vibrational behavior, and chemical reactivity. The optimized geometries and total electronic energies revealed that both the type and position of substituents strongly affect molecular stability, with the <i>p</i>-brominated derivative exhibiting the highest stability at -3886.04 a.u, while the nitro-substituted compound showed enhanced electronic activity. Frontier molecular orbital analysis indicates energy gaps ranging from 4.03 to 4.95&#xa0;eV, suggesting differences in charge-transfer ability and kinetic stability among the compounds studied. Furthermore, global reactivity descriptors indicated that the nitro-substituted derivative exhibits the highest softness and electrophilicity, with a value of 2.96&#xa0;eV for compound <b>9</b>, indicating superior electron-accepting capability. Experimental FT-IR, NMR, and mass spectrometric techniques showed excellent agreement with theoretical predictions, confirming the reliability of the computational model. ELF, LOL, and NCI-RDG analyses provided detailed insight into electron localization and covalent bonding at C–C, C–N, C–O, C–Br, and C–Cl bonds, steric effects near aromatic carbons, and weak intermolecular interactions close to C–O, Cl–O, O–S and C–S links.</p>

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Structural and electronic insights into vanillin sulfonates: a spectroscopic and DFT study

  • 期刊论文

  • 发表日期：

    2026年7月6日

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  • Ahlam Roufieda Guerroudj,
  • Ehsan Ullah Mughal,
  • Nafeesa Naeem,
  • H. A. Alrafai,
  • Abdullah Yahya Abdullah Alzahrani,
  • Maher Fathalla,
  • Mehdi Damou,
  • Abdelkader Chouaih

摘要

Vanillin sulfonate derivatives are an important class of functional organic compounds with promising applications in materials science and molecular design. In this study, vanillin sulfonate derivatives (1–9) bearing halogen (F, Cl, Br), nitro (NO2), and methoxy (OCH3) substituents were investigated using a combined experimental and computational approach. Density functional theory calculations were performed at the B3LYP/6-31G(d, p) level to evaluate their structural stability, electronic properties, vibrational behavior, and chemical reactivity. The optimized geometries and total electronic energies revealed that both the type and position of substituents strongly affect molecular stability, with the p-brominated derivative exhibiting the highest stability at -3886.04 a.u, while the nitro-substituted compound showed enhanced electronic activity. Frontier molecular orbital analysis indicates energy gaps ranging from 4.03 to 4.95 eV, suggesting differences in charge-transfer ability and kinetic stability among the compounds studied. Furthermore, global reactivity descriptors indicated that the nitro-substituted derivative exhibits the highest softness and electrophilicity, with a value of 2.96 eV for compound 9, indicating superior electron-accepting capability. Experimental FT-IR, NMR, and mass spectrometric techniques showed excellent agreement with theoretical predictions, confirming the reliability of the computational model. ELF, LOL, and NCI-RDG analyses provided detailed insight into electron localization and covalent bonding at C–C, C–N, C–O, C–Br, and C–Cl bonds, steric effects near aromatic carbons, and weak intermolecular interactions close to C–O, Cl–O, O–S and C–S links.