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DFT study of the per-6-amino-β-cyclodextrin as catalyst in synthesis of 2-aryl-2,3-dihydro-4-quinolones

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Abstract

The synthesis of 2-aryl-2,3-dihydro-4-quinolones in the presence of per-6-amino-β-cyclodextrin (per-6-ABCD) as catalyst can improve selectivity and yield. The interaction between per-6-ABCD and benzaldehyde or o-aminoacetophenone plays an important role in this reaction. This paper studies the complexes of per-6-ABCD with benzaldehyde and o-aminoacetophenone using density functional theory (DFT) method. The reaction process is investigated by studying the energy of the reactants and the product. Hydrogen bonds are researched on the basis of natural bonding orbital (NBO) analysis, the results propose the donor–acceptor interactions of complex. The Mulliken charge and frontier orbital are employed for revealing the charge distribution. In addition, 13C nuclear magnetic resonance (13CNMR) spectroscopy shows that the carbon atom on the aldehyde group for benzaldehyde, carbonyl group and the carbon atom connected with carbonyl group for o-aminoacetophenone are apparently activated in the cavity of per-6-ABCD. The probable catalytic mechanism of per-6-ABCD is discussed in terms of the calculated parameters.

Per-6-amino-β-cyclodextrin as catalyst in synthesis of 2-aryl-2,3-dihydro-4-quinolones

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Acknowledgment

The authors wish to acknowledge the financial supports from the Scientific Research Fund of Hunan Provincial Education Department (No. 12A132) for the research work.

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  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

    Yali Wan, Xueye Wang & Na Liu

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  1. Yali Wan
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  2. Xueye Wang
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  3. Na Liu
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Correspondence to Xueye Wang.

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Wan, Y., Wang, X. & Liu, N. DFT study of the per-6-amino-β-cyclodextrin as catalyst in synthesis of 2-aryl-2,3-dihydro-4-quinolones. J Mol Model 20, 2431 (2014). https://doi.org/10.1007/s00894-014-2431-1

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  • DOI: https://doi.org/10.1007/s00894-014-2431-1

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