4,4′-azobis(phenylcyanamide)

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4,4′-azobis(phenylcyanamide)
• 化学式: C₁₄H₁₀N₆
• 分子量: 262.274
• InChiKey: KOWFLNCLJKLORJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4′-azobis(phenylcyanamide) 、 在 三乙胺 作用下， 以 甲醇 为溶剂， 以74 %的产率得到
  参考文献：
  名称：

  偶氮-氰酰胺桥联双核铁络合物在两个铁中心之间不表现出电子耦合但具有中等磁耦合

  摘要：

  一系列新型偶氮氰酰胺桥铁配合物已被合成和表征。配合物末端金属铁之间的距离达到18 Å，金属铁之间不存在电子耦合，但存在适度的反铁磁耦合。

  DOI：

  10.1002/cphc.202400009
• 作为产物：
  描述：

  对二氨基偶氮苯 在 正丁基锂 、 碘苯二乙酸 、 氨 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 39.5h， 生成 4,4′-azobis(phenylcyanamide)
  参考文献：
  名称：

  Variable Noninnocence of Substituted Azobis(phenylcyanamido)diruthenium Complexes

  摘要：

  The synthetic chemistry of substituted 4,4'-azobis(phenylcyanamide) ligands was investigated, and the complexes [{Ru(tpy)(bpy)}(2)(mu-L)][PF6](2), where L = 2,2':5,5'-tetramethyl-4,4'-azobis(phenylcyanamido) (Me4adpc(2)), 2,2'-dimethyl-4,4'-azobis(phenylcyanamido) (Me(2)adpc(2)), unsubstituted (adpc2), 3,3'-dichloro-4,4'-azobis(phenylcyanamido) (Cl(2)adpc(2)), and 2,2':5,5'-tetrachloro-4,4'-azobis(phenylcyanamido) (Cl(4)adpc(2)), were prepared and characterized by cyclic voltammetry and visnear-IR (NIR) and IR spectroelectrochemistry. The room temperature electron paramagnetic resonance spectrum of [{Ru(tpy)(bpy)}(2)(mu-Me(4)adpc)](3+) showed an organic radical signal and is consistent with an oxidation-state description [Ru-II, Me(4)adpc, Ru-II](3+), while that of [{Ru(tpy)(bpy)}(2)(mu-Cl(2)adpc)](3+) at 10 K showed a low-symmetry Ru-III signal, which is consistent with the description [Ru-III, Cl(2)adpc(2), Ru-II](3+). IR spectroelectrochemistry data suggest that [{Ru(tpy)(bpy)}(2)(mu-adpc)](3+) is delocalized and [{Ru(tpy)(bpy)}(2)(mu-Cl(2)adpc)](3+) and [{Ru(tpy)(bpy)}(2)(mu-Cl(4)adpc)](3+) are valence-trapped mixed-valence systems. A NIR absorption band that is unique to all [{Ru(tpy)(bpy)}(2)(mu-L)](3+) complexes is observed; however, its energy and intensity vary depending on the nature of the bridging ligand and, hence, the complexes oxidation-state description.

  DOI：

  10.1021/ic502487x

文献信息

• Variable Noninnocence of Substituted Azobis(phenylcyanamido)diruthenium Complexes
  作者：Mohommad M. R. Choudhuri、Mahdi Behzad、Mousa Al-Noaimi、Glenn P. A. Yap、Wolfgang Kaim、Biprajit Sarkar、Robert J. Crutchley

  DOI：10.1021/ic502487x

  日期：2015.2.16

  The synthetic chemistry of substituted 4,4'-azobis(phenylcyanamide) ligands was investigated, and the complexes [Ru(tpy)(bpy)}(2)(mu-L)][PF6](2), where L = 2,2':5,5'-tetramethyl-4,4'-azobis(phenylcyanamido) (Me4adpc(2)), 2,2'-dimethyl-4,4'-azobis(phenylcyanamido) (Me(2)adpc(2)), unsubstituted (adpc2), 3,3'-dichloro-4,4'-azobis(phenylcyanamido) (Cl(2)adpc(2)), and 2,2':5,5'-tetrachloro-4,4'-azobis(phenylcyanamido) (Cl(4)adpc(2)), were prepared and characterized by cyclic voltammetry and visnear-IR (NIR) and IR spectroelectrochemistry. The room temperature electron paramagnetic resonance spectrum of [Ru(tpy)(bpy)}(2)(mu-Me(4)adpc)](3+) showed an organic radical signal and is consistent with an oxidation-state description [Ru-II, Me(4)adpc, Ru-II](3+), while that of [Ru(tpy)(bpy)}(2)(mu-Cl(2)adpc)](3+) at 10 K showed a low-symmetry Ru-III signal, which is consistent with the description [Ru-III, Cl(2)adpc(2), Ru-II](3+). IR spectroelectrochemistry data suggest that [Ru(tpy)(bpy)}(2)(mu-adpc)](3+) is delocalized and [Ru(tpy)(bpy)}(2)(mu-Cl(2)adpc)](3+) and [Ru(tpy)(bpy)}(2)(mu-Cl(4)adpc)](3+) are valence-trapped mixed-valence systems. A NIR absorption band that is unique to all [Ru(tpy)(bpy)}(2)(mu-L)](3+) complexes is observed; however, its energy and intensity vary depending on the nature of the bridging ligand and, hence, the complexes oxidation-state description.
• Azo‐Cyanamide Bridged Dinuclear Iron Complexes Exhibiting no Electronic Coupling but Moderate Magnetic Coupling between the two Iron Centers
  作者：Zhong‐Dong Mao、Jin‐Hui Fu、Yong He、Ying Song、Bing‐Chang Tan、Ling‐Ting Chen、Xin‐Tao Wu、Tian‐Lu Sheng

  DOI：10.1002/cphc.202400009

  日期：2024.4.16

  A series of novel azo-cyanamide bridging iron complexes have been synthesized and characterized. The distance between the metal irons at the ends of the complexes reaches 18 Å, and there is no electronic coupling between the metal irons, but there is moderate antiferromagnetic coupling.

  一系列新型偶氮氰酰胺桥铁配合物已被合成和表征。配合物末端金属铁之间的距离达到18 Å，金属铁之间不存在电子耦合，但存在适度的反铁磁耦合。