| S-（＋）-（E）-1-（2-furfuryl）-5-substituted-1,3,5-hexahydrotriazine-2-N-nitroimines：Synthesis,Crystal Structure and DFT Calculations |
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| 引用本文： | 方庭,步洪飞,薛思佳,刘丽,丁丽,王晶.S-（＋）-（E）-1-（2-furfuryl）-5-substituted-1,3,5-hexahydrotriazine-2-N-nitroimines：Synthesis,Crystal Structure and DFT Calculations[J].结构化学,2011,30(10):1452-1458. |
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| 作者姓名： | 方庭 步洪飞 薛思佳 刘丽 丁丽 王晶 |
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| 作者单位： | Department of Chemistry;College of Life and Environmental Science;Shanghai Normal University; |
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| 基金项目： | supported by the National Natural Science Foundation of China (21042010); the Key Laboratory of Rare Earth Functional Materials of Shanghai (07dz22303); the Key Scientific and Technological Project of Shanghai (09391912100) |
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| 摘 要： | A novel neonicotinoid analogue(C13H19N5O5,3a)had been synthesized,the structure was characterized by elemental analysis,IR and 1H NMR spectra,and the S-(+)-(E)-configuration was confirmed by single-crystal X-ray diffraction.The crystal belongs to monoclinic,space group P21 with a = 8.7076(17),b = 8.3211(17),c = 10.642(2),β = 92.370(3)o,V = 770.4(3)3,Z = 2,Dc = 1.402 g/cm3,μ = 0.110 mm-1,Mr = 325.33,F(000)= 344,S = 1.027,R = 0.0543 and wR = 0.1229 for 3601 unique reflections with 2919 observed ones(I > 2σ(I)).Compound 3a is stabilized by intramolecular hydrogen bonds and intermolecular force.In addition,the structure of compound 3a was optimized by the B3LYP/6-31G(d,p).DFT/B3LYP optimizations were performed based on X-ray geometries applying 6-31G(d,p)basis set.The optimized structure of compound 3a by the B3LYP/6-31G(d,p)method is more bent than in the crystal.IR spectrum of the solid compound is consistent with the X-ray structure.The HOMO-LUMO gap in 3a(5.3 eV)indicates high kinetic stabilities of compound 3a.The preliminary bioassay test showed that 3a exhibited good activities against Nilaparvata legen,Pseudaletia separate Walker and Aphis medicagini at 500 mg/L.
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| 关 键 词： | 晶体结构 DFT计算 合成 动力学稳定性 固体化合物 结构优化 红外光谱 核磁共振谱 |
S-(+)-(E)-1-(2-furfuryl)-5-substituted-1,3,5-hexahydrotriazine-2-N-nitroimines:Synthesis,Crystal Structure and DFT Calculations |
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| FANG Ting
,
BU Hong-Fei
,
XUE Si-Jia
,
LIU Li
,
DING Li
,
WANG Jing.S-(+)-(E)-1-(2-furfuryl)-5-substituted-1,3,5-hexahydrotriazine-2-N-nitroimines:Synthesis,Crystal Structure and DFT Calculations[J].Chinese Journal of Structural Chemistry,2011,30(10):1452-1458. |
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| Authors: | FANG Ting BU Hong-Fei XUE Si-Jia LIU Li DING Li WANG Jing |
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| Institution: | Department of Chemistry, College of Life and Environmental Science, Shanghai Normal University, Shanghai 200234, China |
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| Abstract: | A novel neonicotinoid analogue(C13H19N5O5,3a)had been synthesized,the structure was characterized by elemental analysis,IR and 1H NMR spectra,and the S-(+)-(E)-configuration was confirmed by single-crystal X-ray diffraction.The crystal belongs to monoclinic,space group P21 with a = 8.7076(17),b = 8.3211(17),c = 10.642(2),β = 92.370(3)o,V = 770.4(3)3,Z = 2,Dc = 1.402 g/cm3,μ = 0.110 mm-1,Mr = 325.33,F(000)= 344,S = 1.027,R = 0.0543 and wR = 0.1229 for 3601 unique reflections with 2919 observed ones(I > 2σ(I)).Compound 3a is stabilized by intramolecular hydrogen bonds and intermolecular force.In addition,the structure of compound 3a was optimized by the B3LYP/6-31G(d,p).DFT/B3LYP optimizations were performed based on X-ray geometries applying 6-31G(d,p)basis set.The optimized structure of compound 3a by the B3LYP/6-31G(d,p)method is more bent than in the crystal.IR spectrum of the solid compound is consistent with the X-ray structure.The HOMO-LUMO gap in 3a(5.3 eV)indicates high kinetic stabilities of compound 3a.The preliminary bioassay test showed that 3a exhibited good activities against Nilaparvata legen,Pseudaletia separate Walker and Aphis medicagini at 500 mg/L. |
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| Keywords: | neonicotinoid synthesis crystal structure DFT calculations hexahydrotriazine |
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