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SYNTHESIS, CRYSTAL STRUCTURE, AND DFT STUDY OF METHYL 3-FLUORO-5-(4,4,5,5-TETRAMETHYL-1,3,2- DIOXABOROLAN-2-YL)BENZOATE AND (2-METHYL-4- (4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL) PHENYL)(PYRROLIDIN-1-YL)METHANONE COMPOUNDS

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Abstract

Methyl 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate and (2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)(pyrrolidin-1-yl)methanone are boric acid ester intermediates with benzene rings. In this paper, the title compounds are obtained by a three-step substitution reaction. The structures of the compounds are confirmed by FTIR, 1H and 13C NMR spectroscopy, and mass spectrometry. At the same time, single crystals of the title compounds are measured by X-ray diffraction and subjected to crystallographic and conformational analyses. The molecular structures are further calculated using density functional theory (DFT), which were compared with the X-ray diffraction value. The results of the conformational analysis indicate that the molecular structures optimized by DFT are consistent with the crystal structures determined by single crystal X-ray diffraction. In addition, the molecular electrostatic potential and frontier molecular orbitals of the title compounds are further investigated by DFT, and some physicochemical properties of the compounds are revealed.

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Funding

This work was supported by the Guizhou University of Traditional Chinese Medicine 2018 (annual academic new seedling cultivation and innovation exploration special project, Qiankehe platform talent [2018]5766-14). The theoretical calculations were conducted at the ScGrid and Deepcomp 7000 the Supercomputing Center, Computer Network Information Center of Chinese Academy of Sciences.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Guizhou University, Guiyang, People’s Republic of China

    P. -Y. Huang & D. -Z. Yang

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

    P. -Y. Huang, Z. -S. Yang, Q. -M. Wu, D. -Z. Yang, J. -J. Chen & C. -S. Zhao

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

    Z. -S. Yang, Q. -M. Wu, J. -J. Chen & C. -S. Zhao

  4. College of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang, People’s Republic of China

    H. -F. Chai

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

    C. -S. Zhao

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  1. P. -Y. Huang
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Correspondence to C. -S. Zhao.

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Text © The Author(s), 2021, published in Zhurnal Strukturnoi Khimii, 2021, Vol. 62, No. 6, pp. 913-920.https://doi.org/10.26902/JSC_id74415

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Huang, P.Y., Yang, Z.S., Wu, Q.M. et al. SYNTHESIS, CRYSTAL STRUCTURE, AND DFT STUDY OF METHYL 3-FLUORO-5-(4,4,5,5-TETRAMETHYL-1,3,2- DIOXABOROLAN-2-YL)BENZOATE AND (2-METHYL-4- (4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL) PHENYL)(PYRROLIDIN-1-YL)METHANONE COMPOUNDS. J Struct Chem 62, 845–852 (2021). https://doi.org/10.1134/S0022476621060044

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