Five new difluorinated biphenyl compounds, 4′-(tert-butyl)-3,4-difluoro-1,1′-biphenyl (TBDFBP), 1-(3′,4′-difluoro-[1,1′-biphenyl]-4-yl)ethanone (DFBPE), 3′,4′-difluoro-2,5-dimethoxy-1,1′-biphenyl (DFDMBP), 3,4-difluoro-3′-nitro-1,1′-biphenyl (DFNBP), and (3′,4′-difluoro-[1,1′-biphenyl]-3-yl)(methyl)sulfane (DFBPMS), have been successfully synthesized by the well-known Suzuki–Miyaura coupling with excellent yields averaging 78%. UV–visible, Fourier transform infrared ,and ¹³C NMR and ¹H NMR spectroscopies along with single-crystal X-ray diffraction (SC-XRD) analysis (for TBDFBP and DFBPE) were used for the structure elucidation of the synthesized compounds. The SC-XRD results demonstrated the crystal systems of the studied compounds, TBDFBP and DFBPE, to be monoclinic, and their space groups were found to be P2₁/c. Also, a detailed density functional theory study was performed. The calculated structures for TBDFBP and DFBPE were found to agree quite well with the experimental results. The natural bonding orbital charge analysis suggested that molecules of these compounds should interact quite noticeably with each other in the solid phase and with polar solvent molecules. Molecular electrostatic potential analysis suggests that accumulation of positive and negative potential implies possibility of quite significant dipole–dipole intermolecular interactions in crystals of these compounds, as well as quite strong interactions with polar solvent molecules. The global reactivity parameters analysis suggests all compounds to be quite stable in redox reactions, with the compound DFNBP being relatively more reactive and the compounds TBDFBP and DFDMBP being relatively more stable.

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通过 Pd(0) 催化反应合成的新型氟化联苯化合物：实验和计算研究

五种新的二氟联苯化合物，4′-(叔丁基)-3,4-二氟-1,1′-联苯(TBDFBP)、1-(3′,4′-二氟-[1,1′-联苯] -4-基)乙酮(DFBPE)、3′,4′-二氟-2,5-二甲氧基-1,1′-联苯(DFDMBP)、3,4-二氟-3′-硝基-1,1′-联苯(DFNBP)和 (3′,4′-二氟-[1,1′-联苯]-3-基)(甲基)硫烷(DFBPMS)已通过著名的 Suzuki-Miyaura 偶联成功合成平均收益率高达 78%。紫外可见分光光度计、傅里叶变换红外分光光度计、¹³ C NMR 和¹ H NMR 光谱以及单晶 X 射线衍射 (SC-XRD) 分析（针对TBDFBP 和 DFBPE）用于合成化合物的结构解析。SC-XRD结果表明，所研究的化合物TBDFBP和DFBPE的晶系为单斜晶系，其空间群为P 2 ₁ / c。此外，还进行了详细的密度泛函理论研究。TBDFBP 和 DFBPE的计算结构与实验结果非常吻合。自然键合轨道电荷分析表明，这些化合物的分子在固相中彼此之间以及与极性溶剂分子之间的相互作用应该非常明显。分子静电势分析表明，正负电势的积累意味着这些化合物的晶体中可能存在相当显着的偶极-偶极分子间相互作用，以及与极性溶剂分子存在相当强的相互作用。整体反应性参数分析表明所有化合物在氧化还原反应中都相当稳定，其中化合物DFNBP相对更具反应性，化合物TBDFBP和DFDMBP相对更稳定。