O-nitrosobistrifluormethylhydroxylamin | 359-75-1

• 分子结构分类: 有机化合物 - 有机卤素化合物
• 英文名称: O-nitrosobistrifluormethylhydroxylamin
• 英文别名: O-nitrosobis(trifluoromethyl)hydroxylamine；O-nitroso-N,N-bis-trifluoromethyl-hydroxylamine；O-Nitroso-N,N-bis-trifluormethyl-hydroxylamin；O-Nitroso-N,N-bis-trifluormethyl-hydroxylamin；O-Nitroso-N,N-bis-trifluormethylhydroxylamin；N,N-Bis-trifluormethyl-hydroxylamin-nitrit；N-(Nitrosooxy)-bis(trifluoromethyl)amine；[bis(trifluoromethyl)amino] nitrite
• CAS: 359-75-1
• 化学式: C₂F₆N₂O₂
• 分子量: 198.025
• InChiKey: OZAKSEWYUHBZET-UHFFFAOYSA-N

物化性质

• 沸点：
  16.19°C (rough estimate)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  O-nitrosobistrifluormethylhydroxylamin 生成 Perfluoro-2-azapropen
  参考文献：
  名称：

  Mason, J., Journal of the Chemical Society

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 亚硝酰氯 作用下， 反应 48.0h， 以92%的产率得到O-nitrosobistrifluormethylhydroxylamin
  参考文献：
  名称：

  O-Nitrosobis(trifluoromethyl)hydroxylamine: unexpected conformational properties and an unusually long (CF3)2NO-NO bond. A combined study of the gaseous and solid states

  摘要：

  The conformational properties and the geometric structure of gaseous O-nitrosobis(trifluoromethyl)-hydroxylamine, (CF3)2N-O-N=O, have been studied by infrared spectroscopy, electron diffraction, and ab initio calculations. From the relative intensities and band contours of the two N=O vibrations, a mixture of 80(10)% trans-syn and 20(10)% trans-anti conformers (DELTAG = G(syn) - G(anti) = -0.8(3) kcal/mol) is derived (trans describes the orientation of the O-N bond relative to the CNC bisector and syn/anti refers to the orientation of N=O relative to N-O). Such a mixture of conformers with planar NONO groups is consistent with the electron diffraction intensities. In addition, the compound has been subjected to X-ray crystal structure analysis. In the solid state, only the trans-syn conformer is present. The O-N single bond is unusually long and differs strongly in the two phases: 1.572(21) angstrom in the gaseous state and 1.669 (3) angstrom in the solid state. The results of ab initio calculations depend strongly on the calculational method, especially for the relative energy of the two conformers and for the O-N bond length: DELTAE = E(syn)-E(anti) = -1.8, +0.6, and -3.3 kcal/mol and O-N = 1.527, 1.401, and 1.717 angstrom with HF/3-21G, HF/6-31G*, and MP2/6-31G*, respectively. None of these predictions agrees very well with the experimental results for the gas phase.

  DOI：

  10.1021/ja00068a060

文献信息

• Novel condensation reactions of O-nitrosobis(trifluoromethyl)hydroxylamine and trifluoronitrosomethane with arsine
  作者：H.G. Ang、F.K. Lee

  DOI：10.1016/0022-1139(93)03009-b

  日期：1994.2

  N-Bis(trifluoromethyl)nitroxy-iminoarsine, (CF3)2NONAsH, is formed by a condensation reaction betweenO- nitrosobis(trifluoromethyl)hydroxylamine and arsine. It undergoes reactions with (CF3)2NO to afford (CF3)2NONAsON(CF3)2 and bis(trifluoromethyl)hydroxylamine. Both the iminoarsines (CF3)2NONAsR (RH, (CF3)2NO) undergo addition reactions across the NAs bond with HI to give (CF3)2NONHAsIR. The

  ñ -双（三氟甲基）硝酰基- iminoarsine，（CF 3）2 NONAsH，通过之间的缩合反应形成ø nitrosobis（三氟甲基）羟胺和胂- 。它经历与（CF反应3）2 NO，得到（CF 3）2 NONAsON（CF 3）2和双（三氟甲基）羟胺。两者iminoarsines（CF 3）2 NONAsR（RH，（CF 3）2 NO）经历跨越NAs键与HI加成反应，得到（CF 3）2NONHASIR。三氟亚硝基甲烷与a的反应遵循相似的途径，提供了不稳定的亚氨基CF 3 N = AsH，即使在低温下，该自由基也会通过自由基机理分解。
• Preparation and reactions of mercury(<scp>II</scp>) bistrifluoromethylnitroxide
  作者：H. J. Emeléus、Jean'ne M. Shreeve、P. M. Spaziante

  DOI：10.1039/j19690000431

  日期：——

  Mercury(II) bistrifluoromethylnitroxide has been prepared by reaction of mercury with an excess of liquid bistrifluoromethylnitroxide radical. It is a white crystalline solid which dissociates to mercury and the free radical at 85°. It reacts at room temperature with typical compounds containing B–Cl, C–halogen, Si–Cl, Ge–Cl, and P–Cl bonds to give the corresponding bistrifluoromethylnitroxide derivative

  通过使汞与过量的液态三氟甲基硝基氧自由基反应制备了汞（II）型双三氟甲基硝基氧。它是白色结晶固体，在85°时会分解为汞和自由基。它在室温下与含有B–Cl，C–卤素，Si–Cl，Ge–Cl和P–Cl键的典型化合物反应，以高收率得到相应的双三氟甲基硝基氧衍生物。三（双三氟甲基硝基氧）硼与氟化铯产生1：1的加合物。
• Exchange reactions between O-nitrosobis(trifluoromethyl)hydroxylamine and M(CF3)3 (M = P, As and Sb)
  作者：H.G. Ang、K.K. So

  DOI：10.1016/s0022-1139(00)80912-4

  日期：1985.4

  solid. With tris(trifluoromethyl)stibine, no oxidation nor addition reactions occurred. Instead, [(CF3)2NO]3Sb and [(CF3)NO]2SbCF3 were obtained in high yields. The stoichiometry of the reactions suggests that the additional amounts of bis(trifluoromethyl)nitroxyl groups bonded to antimony are derived from the trifluoromethyl groups bonded to antimony. Mechanisms to rationalise these reactions are proposed

  O-亚硝基双（三氟甲基）羟胺与三（三氟甲基）-膦，-ar基和-二苯乙烯生成新的反应，主要承担相应的双（三氟甲基）亚硝酚衍生物。三（三氟甲基）膦提供（CF 3）2 NOP（O）（CF 3）2和（CF 3）2 NNO。三（三氟甲基）胂还给出（CF 3）2 NNO以高收率，具有较少量的（CF一起3）2个NOAS（CF 3）2，CF 3 NCF 2，COF 2三（三氟甲基）锑，不发生氧化反应或加成反应。而是以高收率获得了[（CF 3）2 NO] 3 Sb和[（CF 3）NO] 2 SbCF 3。反应的化学计量表明，与锑键合的双（三氟甲基）硝基氧基的额外量源自与锑键合的三氟甲基。提出了使这些反应合理化的机制。
• Polyfluorocyclopentadienes. Part III. Diels–Alder reactions of perfluorocyclopentadiene
  作者：R. E. Banks、A. C. Harrison、R. N. Haszeldine、K. G. Orrell

  DOI：10.1039/j39670001608

  日期：——

  6-hexafluorotricyclo[5,2,1,02,6]deca-3,8-diene) in its reaction with cyclopentadiene. The structures of the Diels–Alder adducts were determined by a combination of chemical and spectroscopic methods; the n.m.r. spectra of the adducts are discussed in detail, and a correlation between structure and 19F n.m.r. spectral parameters is presented. No Diels–Alder adducts were obtained when perfluorocyclopentadiene was

  Perfluorocyclopentadiene分担IN的Diels-Alder反应（一）在其热反应的二烯与乙炔二（→二甲基1,2,3,4,7,7-hexafluorobicylo [2,2,1]庚-2,5-二烯5,6-二羧酸酯），乙烯（→ 1,2,3,4,7,7-六氟双环[2,2,1]庚-2-烯），乙炔（→ 1,2,3,4， 7,7-六氟双环[2,2,1]庚2,5-二烯），马来酸酐（→ 1,2,3,4,7,7-六氟双环[2,2,1]庚-2-烯-5,6-酸酐），丁二烯（→ 1,2,3,4,7,7-六氟-5-乙烯基双环[2,2,1]庚-2-烯），降冰片二烯（→ 3的两个立体异构体， 4,5,6,12,12-hexafluorotetracyclo [6,2,1,1 3,6，0 2,7] dodeca-4,9-diene），三氟亚硝基甲烷 →全氟-（3-甲基-2-氧杂-3-氮杂双环[2,2,
• Addition reactions between O-nitrosobis(trifluoromethyl)hydroxylamine and fluorinated olefins
  作者：H.G. Ang、K.K. So

  DOI：10.1016/s0022-1139(00)84981-7

  日期：1985.2

  O-Nitrosobis(trifluoromethyl)hydroxylamine gives addition products at room temperature with 1,1-difluoro-2,2-dichloroethylene and 1,1-difluoro-2-fluoro-2-bromoethylene. No reactions occurred with a few other chlorinated and fluorinated olefins even at elevated temperatures.

  O-亚硝基双（三氟甲基）羟胺在室温下与1,1-二氟-2,2-二氯乙烯和1,1-二氟-2-氟-2-溴乙烯一起生成加成产物。即使在高温下，也没有与其他几种氯化和氟化烯烃发生反应。