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SYNTHESIS, CRYSTAL STRUCTURE, AND DFT STUDY OF 1-(2-BROMOBENZYL)-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE

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Abstract

1-(2-Bromobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole is an organic intermediate with both pyrazole heterocycle and borate functional group. In this paper, the title compound is obtained by the nucleophilic substitution reaction. The structure of the compound is confirmed by FTIR, 1H and 13C NMR spectroscopy, and MS. At the same time, the single crystal of the title compound is measured by X-ray diffraction and is subjected to the crystallographic and conformational analysis. The molecular structure is further calculated using Density Functional Theory (DFT) and compared with the X-ray diffraction value. The results of the conformational analysis indicate that the molecular structure optimized by DFT is consistent with the crystal structure determined by single crystal X-ray diffraction. In addition, the molecular electrostatic potential and frontier molecular orbitals of the title compound are further investigated by DFT, revealing molecular structure characteristics and molecular conformations.

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Funding

This work was supported by Guizhou University of Traditional Chinese Medicine 2018 annual academic new seedling cultivation and innovation exploration special project cultivation project plan. (Qiankehe platform talent [2018]5766-14).

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Authors and Affiliations

  1. School of Pharmaceutical Sciences, Guizhou University, Guiyang, People’s Republic of China

    Z. Yang, P. Huang, J. Chen, Y. Chen & C. Zhao

  2. Guizhou Engineering Laboratory for Synthetic Drugs, Guiyang, People’s Republic of China

    Z. Yang, P. Huang, J. Chen, Y. Chen & C. Zhao

  3. Department of Pharmacy, Guizhou University of Traditional Chinese Medicine, People’s Republic of China

    T. Gao & H. Chai

  4. Key Laboratory of Guizhou for Fermentation Engineering and Biomedicine, Guiyang, People’s Republic of China

    C. Zhao

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  1. Z. Yang
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  2. P. Huang
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  3. J. Chen
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  4. Y. Chen
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  5. T. Gao
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  6. H. Chai
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  7. C. Zhao
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Correspondence to C. Zhao.

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Text © The Author(s), 2021, published in Zhurnal Strukturnoi Khimii, 2021, Vol. 62, No. 6, pp. 997-1006.https://doi.org/10.26902/JSC_id72898

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Yang, Z., Huang, P., Chen, J. et al. SYNTHESIS, CRYSTAL STRUCTURE, AND DFT STUDY OF 1-(2-BROMOBENZYL)-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE. J Struct Chem 62, 928–937 (2021). https://doi.org/10.1134/S0022476621060123

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