期刊文献+

2,2’,4,4’,6,6’-六硝基二联苯的合成、晶体结构与量化计算 被引量:2

Synthesis, crystal structure and theoretical calculation of 2, 2’, 4, 4’, 6, 6’-hexanitrobiphenyl
原文传递
导出
摘要 本文以2,4,6-三硝基氯苯为原料在惰性溶剂硝基苯中经Ullmann缩合反应制备出了标题化合物2,2’,4,4’,6,6’-六硝基二联苯(HNB),通过FT-IR、氢核磁共振谱、质谱、元素分析、X-射线单晶衍射等手段对其进行了表征,根据晶体结构数据使用G09程序对化合物的能量、分子前沿轨道、净电荷、分子静电势及Wiberg键级进行计算。结果表明,该晶体属于三斜晶系,空间群为P-1(2),晶胞参数为:a=8.2552(8)?,b=12.2204(12)?,c=16.3239(15)?,α=98.413(3)°,β=92.635(3)°,γ=104.424(3)°,V=1571.87(30)?~3,μ=0.16 mm^(-1),ρ=1.793 g·cm^(-3),Z=4,F(000)=856.0。标题化合物的两个苯环接近垂直,同时每个苯环上的硝基官能团与苯环不在同一平面。标题化合物的总能量为-1690.06539 a.u.,最高占据轨道能量为-0.31512 a.u.,最低未被占据轨道能量为-0.14872a.u.,前沿轨道能量差为0.1664 a.u.,化合物具有较高的化学稳定性;标题化合物分子键级最小的键为C(5)-N(3)(0.9185)和C(11)-N(6)(0.9185),为分子中易分解点,化合物的量化计算结果与其晶体结构数据相符。 The title compound has been synthesized by the Ullmann condensation reaction with picryl chloride as raw material and characterized by FT-IR, H NMR, mass spectrometry and X-ray diffraction. The quantum chemistry calculation of the tittle compound has been performed by G09W package at the B3LYP/6- 31g (d, p) basis set. The energy, molecular frontier orbital, mulliken atomic charge, molecular electrostatic potential and bond index of the complex has also been discussed. The result shows that the crystal belongs to triclinic system with space group P-1(2) with a= 8.2552 (8) A, b= 12.2204 (12) A, c= 16.3239 (15) A, α= 98.413 (3)°, β= 92.635 (3)°, γ= 104.424 (3)°, V= 1571.87 (30) A3, μ= 0.16 mm-1, ρ= 1.793 g.cm-3, Z= 4, F(000)= 856.0. The crystal structure shows that the two benzene rings are nearly vertical with each other and the nitro groups are not coplanar with the benzene ring. The total energy of the title compound is -1690.06539 a.u. that of HOMO and LUMO is -0.31512 a.u. and -0.14872a.u. respectively, and the energy gap of MOs is 0.1664 a.u., indicating that the compound has good chemical stability. The minimum bond index of the compound is C(5)-N(3) (0.9185) and C(11)-N(6)(0.9185), which represents the easily decomposed part of the compound. The calculated results are in good agreement with the crystal structure data.
作者 杨峰 党鑫 李永祥 郭恒杰 柴笑笑 YANG Feng, DANG Xin, LI Yongxiang, GUO Hengjie and CHAI Xiaoxiao(School of Chemical Engineering and Technology, North University of China, Taiyuan 030051, Shanxi, Chin)
出处 《计算机与应用化学》 CAS 北大核心 2018年第1期72-79,共8页 Computers and Applied Chemistry
关键词 六硝基二联苯 晶体结构 量化计算 hexanitrobiphenyl, crystal structure, quantitative calculation
  • 相关文献

参考文献2

二级参考文献46

  • 1甘孝贤 崔燕军.多硝基苯聚合物的合成.火炸药学报,1999,(3):39-39.
  • 2Redeeker K H, Hagel R. [ J ]. Propellents, Explosives, Pyrotechnics, 1987. 12.
  • 3Psharin I G, Buzykin B J, Nurgation V V, et al. Moisak reaction of sym-trinitrobenzene defimtives with phosphoryl chloride in the presence of pyridine [ J ].Zh.Org.Khim. ,1967, Russian.
  • 4吴晓青 萧忠良 刘幼平.发射药中粘结剂对耐热安全性的影响[J].火炸药学报,1999,(3).
  • 5Makarov V V,Grinevich E A,Lazshev V Z,et al.Method of Obtaining of the 2,4,6,4′,6′,2″,4″,6″-Octanitro-m-terphenyl[P].RU Pat.2,263,654,Gos.Nauchno-Issled.Inst."Kristall",2005.
  • 6Dacon J C.Nonanitroterphenyl[P].U.S.pat.3,755,471,Secretary of the Navy,1973.
  • 7Sitzmann M E.Nonanitroterphenyl[P].U.S.Pat.6,476,280,Secretary of the Navy,2002.
  • 8Dacon J C.2,4,6-Tripicryl-s-triazinel[P].U.S.pat.3,755,321,Secretary of the Navy,1973.
  • 9Dacon J C.2,4,6-Tripicryl-s-triazine,TPT:its Crystallization and Crystal Density Determinations[R].U.S.NTIS Rep.AD-A023464,NTIS Springfield,1976.
  • 10Anonym.The Development of Spacecraft Explosives for the Lyndon B.Johnson Space Center[R].Naval Surf.Weapons Cent.,White Oak,NASA-CR-147547,1976; Chem.Abstr.,1976,85:145386.

共引文献4

同被引文献4

引证文献2

二级引证文献4

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部