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

• 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
• ISSN: 0022-4766; 1573-8779
• DOI: 10.1134/S0022476621060044

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.