Synthesis, crystal structure and vibrational properties studies of 2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)methyl) benzonitrile and N-(3-bromobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)aniline

• Published in: Journal of molecular structure Vol. 1229; p. 129782
• Main Authors: Wu, Qingmei, Chen, Yumei, Chen, Dongmei, Zhou, Zhixu
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05.04.2021
• Subjects: DFT; Phenylboronic acid ester; Vibrational properties; X-ray crystallography analysis; Phenylboronic acid ester; DFT; X-ray crystallography analysis; Vibrational properties
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2020.129782

•The structures optimized by a DFT method were compared with the X-ray structures.•The title compounds of vibrational properties were analyzed.•The molecular surfaces were clearly described by MEP.•The chemical reactivates of the molecules were calculated from HOMO-LUMO energy data.•The interactions and stabilities of the title molecules were investigated by NBO analysis. 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. [Display omitted]