Synthesis, crystal structure, and DFT study of 1-(2-bromobenzyl)- 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

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.