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<p>The present study explores the [2π + 4π] cycloaddition reaction with the participation of a buta-1,3-diene series with sulfur dioxide. This investigation employs the molecular electron density theory (MEDT), using the 6-311G(d,p) basis set coupled with the MPWB1K method. Analysis of SO<sub>2</sub> reactivity reveals a predominance of the monosynaptic basin V(S2) with a population of 3.14 e and asymmetric NBO charges, where sulfur (1.597) acts as an electrophilic site. The study of chemical potentials shows that SO<sub>2</sub> (<i>μ</i> = 5.37 eV) reacts with dienes via polar interactions, primarily targeting the nucleophilic carbons C1 and C7. The activation energies, ranging from 10.44 to 14.95 kcal.mol<sup>−1</sup>, indicate high barriers, with thermodynamically stable products (∆<i>G</i> range from − 7.35 to − 10.45 kcal.mol<sup>−1</sup>). The ELF and QTAIM results reveal complex electronic reorganizations without covalent bonds at the transition states, highlighting significant non-covalent interactions. Among the products, P3 stands out for its high binding affinity (− 6.6 kcal.mol<sup>−1</sup>) and promising ADMET profile, suggesting potential applications in molecular modeling and protein interaction, despite CYP1A2 inhibition.</p>

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Computational investigation on [2π + 4π] cycloaddition mechanisms of buta-1,3-diene derivatives with sulfur dioxide: DFT and in silico study

  • 期刊论文

  • 发表日期：

    2025年1月29日

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  • Moulay Driss Mellaoui,
  • Alejandro Morales-Bayuelo,
  • Abdallah Imjjad,
  • Haydar Mohammad-Salim,
  • Zainab M. Almarhoon,
  • Khalid Abbiche,
  • Aaziz Jmiai,
  • Souad El Issami,
  • Hanane Zejli,
  • Mohammad Shahidul Islam,
  • Mahboob Alam

摘要

The present study explores the [2π + 4π] cycloaddition reaction with the participation of a buta-1,3-diene series with sulfur dioxide. This investigation employs the molecular electron density theory (MEDT), using the 6-311G(d,p) basis set coupled with the MPWB1K method. Analysis of SO2 reactivity reveals a predominance of the monosynaptic basin V(S2) with a population of 3.14 e and asymmetric NBO charges, where sulfur (1.597) acts as an electrophilic site. The study of chemical potentials shows that SO2 (μ = 5.37 eV) reacts with dienes via polar interactions, primarily targeting the nucleophilic carbons C1 and C7. The activation energies, ranging from 10.44 to 14.95 kcal.mol−1, indicate high barriers, with thermodynamically stable products (∆G range from − 7.35 to − 10.45 kcal.mol−1). The ELF and QTAIM results reveal complex electronic reorganizations without covalent bonds at the transition states, highlighting significant non-covalent interactions. Among the products, P3 stands out for its high binding affinity (− 6.6 kcal.mol−1) and promising ADMET profile, suggesting potential applications in molecular modeling and protein interaction, despite CYP1A2 inhibition.