A combined experimental and computational study of 3-bromo-5-(2,5-difluorophenyl) pyridine and 3,5-bis(naphthalen-1-yl)pyridine: Insight into the synthesis, spectroscopic, single crystal XRD, electronic, nonlinear optical and biological properties
A combined experimental and computational study of 3-bromo-5-(2,5-difluorophenyl) pyridine and 3,5-bis(naphthalen-1-yl)pyridine: Insight into the synthesis, spectroscopic, single crystal XRD, electronic, nonlinear optical and biological properties
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DOI：
10.1016/j.molstruc.2018.01.100
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发表时间：
2018-05-15
影响因子：
3.8
通讯作者：
Iqbal, Muhammad
中科院分区：
文献类型：
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作者：
Ghiasuddin;Akram, Muhammad;Iqbal, Muhammad
碳-碳偶联在有机化学合成领域中起着至关重要的作用。用碳-碳偶联法合成了两个新的吡啶衍生物：3-溴-5-(2，5-二氟苯基)吡啶(1)和3，5-二(1-萘基)吡啶(2)，并用X射线衍射仪、光谱技术和密度泛函理论进行了表征。X射线衍射数据与优化后的密度泛函理论研究结果吻合较好。用“TD-DFT/B3LYP/6-311+G(d，p)”理论水平对所研究的化合物(1)和(2)进行了UV-Vis分析。计算的FT-IR和UV-Vis结果与实验结果吻合较好。在B3LYP/6-311+G(d，p)水平上进行了自然键轨道(NBO)研究，得到了最稳定的分子结构。在B3LYP/6-311+G(d，p)理论水平上进行了前线分子轨道(FMO)分析，表明这些分子可能具有生物活性。此外，化合物(1)和(2)的生物活性已被抑制细菌和真菌的实验活性所证实。化合物(1)和(2)的化学反应活性是通过绘制所研究化合物的整个稳定几何构型上的分子静电势(MEP)来指示的。用B3LYP/6-311+G(d，p)方法计算了该化合物的非线性光学性质，发现由于共轭效应，其非线性光学性质大于尿素的值。进一步用二态模型解释了所研究化合物的非线性光学性质。(C)2018爱思唯尔B.V.保留所有权利。
Carbon-carbon coupling play a vital role in the synthetic field of organic chemistry. Two novel pyridine derivatives: 3-bromo-5-(2,5-difluorophenyl)pyridine (1) and 3,5-bis(naphthalen-1-yl)pyridine (2) were synthesized via carbon-carbon coupling, characterized by XRD, spectroscopic techniques and also investigated by using density functional theory (DFT). XRD data and optimized DFT studies are found to be in good correspondence with each other. The UV-Vis analysis of compounds under study i.e. (1) and (2) was obtained by using "TD-DFT/B3LYP/6-311 + G(d,p)" level of theory to explain the vertical transitions. Calculated FT-IR and UV-Vis results are found to be in good agreement with experimental FT-IR and UV-Vis findings. Natural bond orbital (NBO) study was performed using B3LYP/6-311 + G(d,p) level to find the most stable molecular structure of the compounds. Frontier molecular orbital (FMO) analysis were performed at B3LYP/6-311 + G(d,p) level of theory, which indicates that the molecules might be bioactive. Moreover, the bioactivity of compounds (1) and (2) have been confirmed by the experimental activity in terms of zones of inhibition against bacteria and fungus. Chemical reactivity of compounds (1) and (2) was indicated by mapping molecular electrostatic potential (MEP) over the entire stabilized geometries of the compounds under study. The nonlinear optical properties were computed with B3LYP/6-311 + G(d,p) level of theory which are found greater than the value of urea due to conjugation effect. Two state model has been further employed to explain the nonlinear optical properties of compounds under investigation. (C) 2018 Elsevier B.V. All rights reserved.