The reactivity of phenancyl bromide under β-cyclodextrin as supramolecular catalyst: a computational survey

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• 作者：Yali Wan ; Xueye Wang ; Na Liu
• 关键词：β ; Cyclodextrin (β ; CD) ; Density functional theory (DFT) ; Inclusion complex ; Phenacyl bromide ; Supramolecular catalyst
• 刊名：Journal of Molecular Modeling
• 出版年：2015
• 出版时间：May 2015
• 年：2015
• 卷：21
• 期：5
• 全文大小：1,028 KB
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• 作者单位：Yali Wan (1)
  Xueye Wang (1)
  Na Liu (1)
  
  1. Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, Hunan, 411105, People’s Republic of China
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Computer Applications in Chemistry
  Biomedicine
  Molecular Medicine
  Health Informatics and Administration
  Life Sciences
  Computer Application in Life Sciences
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：0948-5023

文摘

Phenacyl bromide as one starting material in multicomponent reactions (MCRs) with β-cyclodextrin (β-CD) as catalyst can get an excellent yield in short reaction times. The interaction of β-CD with phenacyl bromide plays an important role in this process. This paper studies the complex of β-CD with phenacyl bromide using density functional theory (DFT) method. Energy is investigated to find out the lowest energy of two possible complexation models. Hydrogen bonds are researched on the basis of natural bonding orbital (NBO) analysis. The relative position between phenacyl bromide and β-CD is confirmed by 1H nuclear magnetic resonance (1HNMR). The results of frontier molecular orbitals and charge distribution reveal that β-CD catalyst improves the reactivity and electrophilicity of phenacyl bromide, meanwhile, the carbonyl group of phenacyl bromide more easily gives a carbocationic intermediate in the presence of β-CD as catalyst. The reactivity of phenancyl bromide under β-CD as supramolecular catalysis is improved.