In this present work, the title compounds 2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenoxy)methyl)benzonitrile (A) and N-(3-bromobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2 -dioxaborolan-2-yl)aniline (B) were synthesized and their structure were characterized by spectroscopy (FT-IR, ¹H NMR, ¹³C NMR and MS). The single crystals of the title compounds were confirmed by X-ray diffraction, and the optimized molecular crystal structures were determined based on DFT calculations using B3LYP/6–311 G (2d, p) basis set, which were compared with the X-ray diffraction. The results of the conformation analysis indicated that the molecular structure optimized by DFT were consistent with the crystal structure determined by X-ray single crystal diffraction. DFT and TD-DFT calculations at B3LYP/6-311G (2d, p) level of theory were performed for comparative analysis of spectroscopic data (UV-Visible, ¹³C NMR), geometrical parameters, MEP, FMO and NBO analysis. Furthermore, reliable vibrational assignments which have been made on the basis of characteristic vibratinonal absorption bands of the title compounds.