chlorotricyanomethane | 13883-23-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: chlorotricyanomethane
• 英文别名: chloromethanetricarbonitrile
• CAS: 13883-23-3
• 化学式: C₄ClN₃
• 分子量: 125.517
• InChiKey: NHDXTLYNTJHHQS-UHFFFAOYSA-N

物化性质

• 熔点：
  46-47 °C
• 沸点：
  165.4±35.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  chlorotricyanomethane 在 五溴化磷 作用下， 以 乙醚 为溶剂， 生成 (1-Chloro-2,2-dicyanovinyl)phosphorimidic tribromide
  参考文献：
  名称：

  Kukhar',V.P.; Pavlenko,N.G., Journal of general chemistry of the USSR, 1978, vol. 48, p. 711 - 713

  摘要：

  DOI：
• 作为产物：
  描述：

  potassium tricyanomethide 在 苯膦酰二氯 、 磺酰氯 作用下， 以 环丁砜 为溶剂， 以51%的产率得到chlorotricyanomethane
  参考文献：
  名称：

  Improved Syntheses of Chlorotricyanomethane and Carbamoylchlorodicyanomethane

  摘要：

  Improved procedures for the synthesis of chlorotricyanomethane by reaction of potassium tricyanomethanide with sulfuryl chloride in sulfolane and of carbamoylchlorodicyanomethane by reaction of potassium carbamoyldicyanomethanide with sulfuryl chloride in dichloromethane are described.

  DOI：

  10.1080/00397919708007302

文献信息

• Generation of tricyanomethyl spin adducts of α-phenyl-N-tert-butylnitrone (PBN) via non-conventional mechanisms
  作者：Lennart Eberson、John J. McCullough

  DOI：10.1039/a704634k

  日期：——

  Spin adducts, formally derived from tricyanomethyl radical attachment to α-phenyl-N-tert-butylnitrone (PBN; IUPAC name: N-benzylidene-tert-butylamine N-oxide), have been generated by various methods, such as oxidation of a mixture of tricyanomethanide ion and PBN by tris(4-bromophenyl)aminium ion or bromine, photo-oxidation of a mixture of tricyanomethane and PBN with 2,4,6-tris(4-methoxyphenyl)pyrylium ion as a sensitizer, or photolysis of chlorotricyanomethane and PBN at –30 °C, the low temperature being necessary to avoid fast concurrent cycloaddition with PBN. Both the C- and N-connected spin adducts, (NC)3C-PBN˙ and (NC)2CCN–PBN˙, have been characterized, as has an aminoxyl formed by elimination of hydrogen cyanide from the former species, (NC)2CC(Ph)N(O˙)But. For comparison, similar experiments have been performed using carbamoyldicyanomethanide ion and carbamoylchlorodicyanomethane and the spin adduct H2NCO(CN)2C-PBN˙ has been characterized.The redox properties of tricyanomethanide ion, carbamoyldicyanomethanide ion, chlorotricyanomethane and carbamoylchlorodicyanomethane have been studied by cyclic voltammetry. For chlorotricyanomethane, the redox reactivity has also been evaluated by its propensity to generate radical cations from aromatic substrates ArH in 1,1,1,3,3,3-hexafluoropropan-2-ol. Tricyanomethanide ion has E[(CN)3C˙/(CN)3C–]rev at 1.35 V (vs. Ag/AgCl) in acetonitrile while chlorotricyanomethane with Epc at about 0.6 V and a capability to oxidize compounds with redox potentials up to ca. 1.5 V to radical cations, emerges as belonging to the strongest neutral organic electron acceptors.

  三氰基甲烷与δ-苯基-N-叔丁基硝酮（PBN；IUPAC 名称：三氰基甲烷离子和 PBN 的混合物被三(4-溴苯基)铵离子或溴氧化，三氰基甲烷和 PBN 的混合物与 2、4,6-三(4-甲氧基苯基)吡鎓离子作为敏化剂进行光氧化，或者在±30 °C下对三氯氰基甲烷和 PBN 进行光解，低温是避免与 PBN 同时发生快速环化反应所必需的。(NC)3C-PBNË和(NC)2CCNâPBNË这两种C-和N-连接的自旋加合物以及由前一种物质中的氰化氢消除形成的氨基己基((NC)2CC(Ph)N(OË)But)都已得到表征。通过循环伏安法研究了三氰基甲烷离子、氨基甲酰基二氰基甲烷离子、氯三氰基甲烷和氨基甲酰基氯二氰基甲烷的氧化还原特性。对于三氰基甲烷，还通过其在 1,1,1,3,3,3-hexafluoropropan-2-ol 中从芳香底物 ArH 生成自由基阳离子的倾向评估了其氧化还原反应性。三氰基甲烷离子在乙腈中的 E[(CN)3CË/(CN)3Câ]rev 值为 1.35 V（相对于 Ag/AgCl），而三氯氰基甲烷的 Epc 值约为 0.6 V，能够将氧化还原电位高达约 1.5 V 的化合物氧化为自由基阳离子，是最强的中性有机电子受体。
• Kukhar',V.P. et al., Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 306 - 308
  作者：Kukhar',V.P. et al.

  DOI：——

  日期：——
• Kukhar',V.P. et al., Journal of general chemistry of the USSR, 1973, vol. 43, p. 1883 - 1886
  作者：Kukhar',V.P. et al.

  DOI：——

  日期：——
• Oxidation of the Tricyanomethanide ion: the tricyanocarbonium ion
  作者：R.C. Beaumont、K.B. Aspin、T.J. Demas、J.H. Hoggatt、G.E. Potter

  DOI：10.1016/s0020-1693(00)82399-3

  日期：1984.5
• Eberson, Lennart; McCullough, John J.; Hartshorn, Chris, M., Journal of the Chemical Society. Perkin transactions II, 1998, # 1, p. 41 - 48
  作者：Eberson, Lennart、McCullough, John J.、Hartshorn, Chris, M.、hartshorn, Michael P.

  DOI：——

  日期：——