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
| Autor: | J.-J. Chen, Z.-S. Yang, D. Z. Yang, Qingmei Wu, P.-Y. Huang, Huifang Chai, Chunshen Zhao |
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| Rok vydání: | 2021 |
| Předmět: |
Substitution reaction
Crystal structure 010402 general chemistry 010403 inorganic & nuclear chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound chemistry X-ray crystallography Materials Chemistry Molecular orbital Density functional theory Physical and Theoretical Chemistry Fourier transform infrared spectroscopy Benzene Single crystal |
| Zdroj: | Journal of Structural Chemistry. 62:845-852 |
| ISSN: | 1573-8779 0022-4766 |
| DOI: | 10.1134/s0022476621060044 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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