Synthesis, crystal and molecular structures, DFT calculations, spectroscopic (IR, NMR, UV–Vis), vibrational properties and Hirshfeld surface and antitumor activity of two pyrazole boronic acid pinacol ester compounds

Abstract

In this study, title compounds 1-(cyclopropylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (A) and N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-sulfonamide (B) were synthesized by a one-step reaction, and their structures were determined using FT-IR, 1H NMR, 13C NMR spectra, MS and X-ray single crystal diffraction, and the crystallography and conformational analysis were performed. The optimal structure and front-line orbital energies of compounds A and B were determined using density functional theory (DFT) in the B3LYP/6-311+G(2d, p) mode. In addition, we compared and analyzed the spectral data (13C NMR, 1H NMR, and UV–visible) by DFT and TD-DFT calculations, and studied the molecular electrostatic potential, frontier molecular orbital, vibration analysis, and Hirshfeld surface analysis of the title compounds. Finally, the proliferative effects of compounds A and B were evaluated.