2-cyano-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide | 21431-62-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-cyano-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide
• CAS: 21431-62-9
• 化学式: C₈H₁₂N₃O₂
• 分子量: 182.202
• InChiKey: KMEKNVXKGZYKPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-cyano-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide 在 sodium azide 、 氯化铵 、 溶剂黄146 、 sodium nitrite 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 4,4,5,5-tetramethyl-2-(1-methyl-1H-tetrazol-5-yl)-4,5-dihydro-1H-imidazole 1-oxide
  参考文献：
  名称：

  铜 (II) 双（六氟乙酰丙酮）与 2-(2-甲基四唑基)-4,4,5,5-四甲基-4,5-二氢-1H-咪唑 1-氧化物络合物

  摘要：

  开发了一种有效的方法来合成烷基四唑基取代的硝酰基氮氧化物（L1 和 L2）。这些化合物用于制备第一个烷基四唑基取代的亚氨基氮氧化物（L3 和 L4）。L3和L4的分子结构由X射线衍射证实。对通过双（六氟乙酰丙酮）铜 (II)、Cu(hfac)2 与氮氧化物反应制备的产物进行研究，可以将配体 L1-L4 分为两组。自旋标记的四唑 L1-L3 与 Cu(hfac)2 的反应提供了异自旋配合物 Cu(hfac)2L2，而 L4 作为 Cu(hfac)2L4 配合物中的双齿配体。在固体 Cu(hfac)2L2 复合物中，相邻分子的氮氧化合物碎片的未成对电子之间的反铁磁交换相互作用占主导地位，

  DOI：

  10.1007/s11172-006-0216-0
• 作为产物：
  描述：

  4,4,5,5-tetramethylimidazolin-1-oxyl-3-oxide 在 溴化氰 、 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 2-cyano-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide
  参考文献：
  名称：

  摘要：

  Crystal and molecular structure of the nitroxide 2-cyano-4,4,5,5-tetramethyl-3-oxide-2-imidazoline-1-oxyl it-as studied The nontrivial features of the structure are coplanarity of all atoms of the 2-imidazoline heterocycle and the nitrile group bonded to it and short intermolecular contacts between the nitroxyl O atoms and the C atoms in the 2 position of the heterocycles of the neighboring molecules, actually forming layers in the crystal structure. These data agree with the results of magnetic studies,, which are well approximated by the two-dimensional model, which is a rare occurrence for organic magnets.

  DOI：

  10.1023/a:1017933803737

文献信息

• Addition of cyanomethyl anion to the cyano group of 2-cyano-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl, a nitronyl nitroxide
  作者：Evgeny V. Tretyakov、Roman Yu. Peshkov、Elena V. Panteleeva、Andrey S. Scrypnik、Dmitri V. Stass、Galina V. Romanenko、Victor I. Ovcharenko

  DOI：10.1016/j.tetlet.2016.04.070

  日期：2016.5

  Crystallization provided at least two polymorphs of the synthesized nitroxide according to single crystal X-ray data. ESR spectroscopy revealed delocalization of unpaired electron spin density into the enaminonitrile substituent. The synthesized nitronyl nitroxide is of interest for the preparation of new polyfunctional nitroxides and as polydentate paramagnetic ligands.

  在2-氰基-4,4,5,5-四甲基-4,5-二氢-1 H-咪唑-3-氧化物-1-氧基中将氰甲基阴离子加到氰基的三键上，形成稳定的（Z）-3-氨基-3-（4,4,5,5-四甲基-4,5-二氢-1 H报道了-咪唑-3-氧化物-1-氧基-2-基）丙烯腈。产物的产率取决于氰基甲基阴离子盐的抗衡离子，并且在液态氨中的钾盐情况下产率最高。根据单晶X射线数据，结晶提供了合成氮氧化物的至少两个多晶型物。ESR光谱显示未成对的电子自旋密度离域为对氨基腈取代基。合成的硝酰基硝基氧对于制备新的多官能氮氧化物和作为多齿顺磁性配体很重要。
• The Cyano Nitronyl Nitroxide Radical: Experimental and Theoretical Evidence for the Fourth Case of the McConnell-I Mechanism
  作者：Catherine Hirel、Dominique Luneau、Jacques Pécaut、Lars Öhrström、Guillaume Bussière、Christian Reber

  DOI：10.1002/1521-3765(20020715)8:14<3157::aid-chem3157>3.0.co;2-f

  日期：2002.7.15

  The nitronyl nitroxide 2-cyano-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide (1) crystallises in the tetragonal P (4) over bar2(1)m space group with a = 7.4050(7), c = 8.649(1) Angstrom. In the crystal the molecules form layers parallel to the ab plane in which they are orthogonal to each other. In the layers there are close contacts, 2.953(2) Angstrom, between the NO groups and the bridging carbon atoms of the O-N-C-N-O fragment of neighbouring radicals. The calculated spin density shows a positive population mainly and equally localised on the NO groups and small but significant negative spin densities on the bridging carbon atom and the cyano nitrogen. Absorption spectra show temperature-dependent transitions related to the magnetic behaviour. The temperature dependence of the magnetic susceptibility in the range 2-300 K reveals that couplings between the radicals are antiferromagnetic, and is interpreted by considering a two-dimensional square array of spin S = 1/2 antiferromagnetically coupled (J = -10 cm(-1) and g = 2.01). This is interpreted as an exchange coupling through close contact between positive and negative spin densities in orthogonal orbitals on oxygen and carbon atoms, respectively.
• Esters of 4,5-dihydro-1H-imidazole-1-oxyl-3-oxide-carboximidic acid
  作者：E. V. Tretyakov、G. V. Romanenko、Yu. G. Shvedenkov、V. I. Ovcharenko、R. Z. Sagdeev

  DOI：10.1023/b:rucb.0000042290.30451.67

  日期：2004.6

  Esters of 4,5-dihydro-1H-imidazole-1-oxyl-3-oxide-carboximidic acid were synthesized. Their structures and magnetic properties were investigated.