bis(p-chlorophenyl)sulfur diimide | 2648-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(p-chlorophenyl)sulfur diimide
• 英文别名: N,N'-bis-(4-chloro-phenyl)-sulfur diimide；Bis-schwefeldiimid；Di-<4-chlor-phenyl>-sulfurdiimin；N.N'-Di-(p-Chlorphenyl)schwefeldiimid；Bis-(4-chlor-phenyl)-schwefeldiimid；N,N'-Di-p-chlorphenylschwefeldiimid；C12H8Cl2N2S；bis[(4-chlorophenyl)imino]-λ4-sulfane
• CAS: 2648-43-3；57083-07-5；57155-78-9
• 化学式: C₁₂H₈Cl₂N₂S
• 分子量: 283.181
• InChiKey: WLSSXCBGXXZGJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis(p-chlorophenyl)sulfur diimide 以 四氯化碳 、 二氯甲烷 为溶剂， 生成 1-(4-chloro-N-ethyl-anilino)-2,5-bis-(4-chloro-phenyl)-3,4-dioxo-[1,2,5]thiadiazolidinium; tetrafluoroborate
  参考文献：
  名称：

  Neidlein,R. et al., Chemische Berichte, 1977, vol. 110, p. 3149 - 3160

  摘要：

  DOI：
• 作为产物：
  描述：

  N-亚磺酰-4-氯苯胺 在 potassium tert-butylate 作用下， 生成 bis(p-chlorophenyl)sulfur diimide
  参考文献：
  名称：

  Carpanelli, Corrado; Gaiani, Giovanni, Gazzetta Chimica Italiana, 1983, vol. 113, # 7/8, p. 503 - 506

  摘要：

  DOI：

文献信息

• Rapid and Effective Synthesis of Diarylsulfur Diimides from Substituted Anilines and Sulfur Monochloride
  作者：Oleg Rakitin、Lidia Konstantinova、Kirill Lysov

  DOI：10.1055/s-0032-1318140

  日期：——

  Abstract A one-pot and effective procedure has been developed for the synthesis of symmetrical diarylsulfur diimides from anilines, sulfur monochloride, and DABCO in good yields (70–90%). A plausible mechanism for this transformation has been proposed. A one-pot and effective procedure has been developed for the synthesis of symmetrical diarylsulfur diimides from anilines, sulfur monochloride, and DABCO

  摘要 已经开发了一种一锅有效的方法，可以以良好的收率（70-90％）从苯胺，一氯化硫和DABCO合成对称的二芳基硫二酰亚胺。已经提出了这种转变的合理机制。 已经开发了一种一锅有效的方法，可以以良好的收率（70-90％）从苯胺，一氯化硫和DABCO合成对称的二芳基硫二酰亚胺。已经提出了这种转变的合理机制。
• N,N’‐Diaryl‐Sulfurdiimides are Strongly Redox Tuned
  作者：Nathan D. D. Hill、René T. Boeré

  DOI：10.1002/chem.202400563

  日期：——

  The synthesis and extensive characterization of nine aryl sulfur diimides (SDIs, Ar−NSN−Ar) are presented with a robust computational and experimental investigation of the fundamental properties of these important members of the thiazyl family of compounds, with particular attention paid to their highly tunable electrochemical behaviour. This is the first work to undertake a systematic comparison of the electrochemical profiles of a coherent series of SDIs to demonstrate and quantify the response of their reduction potentials to substituent electron‐donating and ‐withdrawing properties. This effect is found to be not only exceptionally strong, but also correlates very closely with computed orbital energies. Electron paramagnetic resonance spectroscopy is used to determine the nature, localization, and qualitative lifetimes of the radical anions of SDIs. This work also addresses significant misconceptions about physical properties of SDIs. Experimental data and modern computational methods are employed to provide a resolute answer to the long‐standing contention of the solution‐state conformations of SDIs, and to correct historical mistakes in the assignment of infrared spectroscopic data. High‐quality crystal structures of all SDIs in this work showcase the utility of the recently introduced structural refinement software NoSpherA2, enabling full anisotropic refinement of H‐atoms with accurate C−H bond lengths.

  摘要 本文介绍了九种芳基硫二亚胺（SDIs，Ar-NSN-Ar）的合成和广泛表征，并对这些噻唑族化合物重要成员的基本性质进行了深入的计算和实验研究，尤其关注它们高度可调的电化学行为。这是首次对一系列连贯的 SDI 的电化学特性进行系统比较，以展示和量化它们的还原电位对取代基电子供取特性的响应。研究发现，这种效应不仅异常强烈，而且与计算出的轨道能量密切相关。电子顺磁共振光谱法用于确定 SDIs 自由基阴离子的性质、定位和定性寿命。这项研究还解决了有关 SDI 物理性质的重大误解。通过实验数据和现代计算方法，对 SDIs 溶液态构象的长期争论给出了明确的答案，并纠正了红外光谱数据赋值方面的历史性错误。这项研究中所有 SDIs 的高质量晶体结构都展示了最近推出的结构细化软件 NoSpherA2 的实用性，该软件可以对具有精确 C-H 键长度的 H 原子进行完全各向异性细化。
• Synthesis of symmetrical bis(aryl)sulfur diimides
  作者：Yi Xiang Ding、William P. Weber

  DOI：10.1021/jo00229a041

  日期：1987.10
• Reactions of sulfurdiimines and sulfinylanilines with [AlMe3]2
  作者：J.M. Klerks、R. Van Vliet、G. Van Koten、K. Vrieze

  DOI：10.1016/s0022-328x(00)85950-1

  日期：1981.6
• The stereochemical outcome of diene additions to thionitrosoarenes (ArN=S)
  作者：Martin R. Bryce、Paul C. Taylor

  DOI：10.1016/s0040-4039(01)80671-7

  日期：1989.1