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

IF 2.2 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
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
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引用次数: 0

Abstract

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.

丁-1,3-二烯衍生物与二氧化硫[2π + 4π]环加成机理的计算研究:DFT和硅研究
本研究探讨了丁-1,3-二烯系与二氧化硫参与的[2π + 4π]环加成反应。本研究采用分子电子密度理论(MEDT),采用6-311G(d,p)基集结合MPWB1K方法。SO2反应性分析表明,单突触盆地V(S2)占主导地位,其种群为3.14 e和不对称NBO电荷,其中硫(1.597)作为亲电位点。化学势研究表明,SO2 (μ = 5.37 eV)通过极性相互作用与二烯发生反应,主要针对亲核碳C1和C7。活化能范围为10.44 ~ 14.95 kcal.mol−1,表明具有较高的势垒,产物热力学稳定(∆G范围为−7.35 ~−10.45 kcal.mol−1)。ELF和QTAIM结果揭示了在过渡态没有共价键的复杂电子重组,突出了显著的非共价相互作用。在这些产品中,P3因其高结合亲和力(−6.6 kcal.mol−1)和有前景的ADMET谱而脱颖而出,这表明尽管CYP1A2具有抑制作用,但在分子建模和蛋白质相互作用方面具有潜在的应用前景。
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来源期刊
Structural Chemistry
Structural Chemistry 化学-化学综合
CiteScore
3.80
自引率
11.80%
发文量
227
审稿时长
3.7 months
期刊介绍: Structural Chemistry is an international forum for the publication of peer-reviewed original research papers that cover the condensed and gaseous states of matter and involve numerous techniques for the determination of structure and energetics, their results, and the conclusions derived from these studies. The journal overcomes the unnatural separation in the current literature among the areas of structure determination, energetics, and applications, as well as builds a bridge to other chemical disciplines. Ist comprehensive coverage encompasses broad discussion of results, observation of relationships among various properties, and the description and application of structure and energy information in all domains of chemistry. We welcome the broadest range of accounts of research in structural chemistry involving the discussion of methodologies and structures,experimental, theoretical, and computational, and their combinations. We encourage discussions of structural information collected for their chemicaland biological significance.
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