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

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 r...

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Bibliographic Details
Published in:Journal of structural chemistry 2021-06, Vol.62 (6), p.845-852
Main Authors: Huang, P. -Y., Yang, Z. -S., Wu, Q. -M., Yang, D. -Z., Chen, J. -J., Chai, H. -F., Zhao, C. -S.
Format: Article
Language:English
Subjects:
Atomic
Atomic/Molecular Structure and Spectra
Benzene
Benzoates
Chemistry
Chemistry and Materials Science
Conformational analysis
Crystal structure
Crystallography
Crystals
Density functional theory
Inorganic Chemistry
Mass spectrometry
Molecular
Molecular orbitals
Molecular structure
NMR spectroscopy
Optical and Plasma Physics
Physical Chemistry
Single crystals
Solid State Physics
Substitution reactions
X-ray diffraction
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Summary: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, 1 H and 13 C 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.
ISSN:0022-4766
1573-8779
DOI:10.1134/S0022476621060044