X-ray Structure and Density Functional Theory Investigations of 4-((2R)-2-(3,4-dibromophenyl)-1-fluoro cyclopropyl)-N-(o-tolyl)benzamide Compound

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摘要 In this work, the structure of 4-((2R)-2-(3,4-dibromophenyl)-1-fluorocyclopropyl)-N-(o-tolyl) benzamide (DBFB) has been determined at room temperature using single-crystal X-ray diffraction data. The structure of the compound was solved using 1464 observed reflections with I ≥ 2σ(I). It crystallizes in monoclinic space group P21 with a = 20.0820(10), b = 10.2770(10), c = 4.860(2) Å, β = 95.9600(10)°, V = 997.6(4) Å3, Z = 2, Dc = 1.675 g/m3, F(000) = 500, Μr = 503.18, μ = 4.09 mm-1 and the final R = 0.0639. The molecular packing of the title compound exhibits C–H⋅⋅⋅O and C–H⋅⋅⋅F hydrogen bonds forming a supramolecular network. Furthermore, conformational analysis has been performed in order to confirm the most stable conformer of the title compound. Geometrical parameters of the keto conformer in the ground state have been obtained using density functional theory (DFT) method with B3LYP/6-31G(d,p) level of theory. In general, a good agreement between the calculated and experimental results was observed. The normal modes of vibration, molecular boundary orbitals (HOMO and LUMO), reactivity descriptors, Mullikan atomic charges and molecular electrostatic potential for the title compound have been evaluated and discussed.

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关键词 ： C₂₃H₁₈Br₂FNO, insecticide, crystal structure, DFT, HOMO-LUMO

Abstract：In this work, the structure of 4-((2R)-2-(3,4-dibromophenyl)-1-fluorocyclopropyl)-N-(o-tolyl) benzamide (DBFB) has been determined at room temperature using single-crystal X-ray diffraction data. The structure of the compound was solved using 1464 observed reflections with I ≥ 2σ(I). It crystallizes in monoclinic space group P21 with a = 20.0820(10), b = 10.2770(10), c = 4.860(2) Å, β = 95.9600(10)°, V = 997.6(4) Å3, Z = 2, Dc = 1.675 g/m3, F(000) = 500, Μr = 503.18, μ = 4.09 mm-1 and the final R = 0.0639. The molecular packing of the title compound exhibits C–H⋅⋅⋅O and C–H⋅⋅⋅F hydrogen bonds forming a supramolecular network. Furthermore, conformational analysis has been performed in order to confirm the most stable conformer of the title compound. Geometrical parameters of the keto conformer in the ground state have been obtained using density functional theory (DFT) method with B3LYP/6-31G(d,p) level of theory. In general, a good agreement between the calculated and experimental results was observed. The normal modes of vibration, molecular boundary orbitals (HOMO and LUMO), reactivity descriptors, Mullikan atomic charges and molecular electrostatic potential for the title compound have been evaluated and discussed.

Key words： C₂₃H₁₈Br₂FNO insecticide crystal structure DFT HOMO-LUMO

收稿日期: 2019-11-04 出版日期: 2020-09-11

通讯作者: achouaih@gmail.com E-mail: achouaih@gmail.com

引用本文:

BENELHADJ-DJELLOUL Yamina;BOUKABCHA Nourdine;BENHALIMA Nadia;YAHIAOUI Salem;CHOU. X-ray Structure and Density Functional Theory Investigations of 4-((2R)-2-(3,4-dibromophenyl)-1-fluoro cyclopropyl)-N-(o-tolyl)benzamide Compound[J]. 结构化学, 2020, 39(9): 1601-1614.
BENELHADJ-DJELLOUL Yamina;BOUKABCHA Nourdine;BENHALIMA Nadia;YAHIAOUI Salem;CHOUAIH Abdelkader;ZANOUN Abdelouahab. X-ray Structure and Density Functional Theory Investigations of 4-((2R)-2-(3,4-dibromophenyl)-1-fluoro cyclopropyl)-N-(o-tolyl)benzamide Compound. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2020, 39(9): 1601-1614.

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http://manu30.magtech.com.cn/jghx/CN/ 或 http://manu30.magtech.com.cn/jghx/CN/Y2020/V39/I9/1601

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