α-acetyl-α-phenylazo-4-chlorophenylazomethine | 891523-25-4

• 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: α-acetyl-α-phenylazo-4-chlorophenylazomethine
• 英文别名: 1-(4-chlorophenylimino)-1-(phenylhydrazono)-propan-2-one；C6H5NNC(COCH3)N(4-chlorophenyl)；N'-(4-chlorophenyl)-2-oxo-N-phenyliminopropanimidamide
• CAS: 891523-25-4
• 化学式: C₁₅H₁₂ClN₃O
• 分子量: 285.733
• InChiKey: VFVSUDSQTITVGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-acetyl-α-phenylazo-4-chlorophenylazomethine 、 三氯化钌 、 1,2-双(二苯基膦)乙烷 在 LiCl 作用下， 以 not given 为溶剂， 生成 cis-[Ru(1,2-bis(diphenylphosphino)ethane)(1-(4-chlorophenylimino)-1-(phenylhydrazono)-propan-2-one)Cl2]
  参考文献：
  名称：

  X-ray structure and DFT study of neutral mixed phosphine azoimine complexes of ruthenium

  摘要：

  Geometry optimization for a cis-[Ru-II(dppe)LCl2] (1-8) {L = C6H5N=NC(COCH3)=NAr, Ar = 2,4,6-trimethylphenyl (L-1), 2,5-dimethylphenyl (L-2), 4-tolyl (L-3), phenyl (L-4), 4-methoxyphenyl (L-5), 4-chlorophenyl (L-6) 4-nitrophenyl (L-7), 2,5-dichlorophenyl (L-8); dppe = Ph2P(CH2)(2)PPh2} was effected using the GAUSSIAN 03 protocol at density functional theory (DFT) B3LYP level with 6-31G*/lanl2dz mixed basis. In addition, the complex cis-[Ru-II(dppe)L3Cl2] (3) has been further characterized by X-ray diffraction analysis. It was found that the optimized structure using 6-31G*/lanl2dz has a large agreement with the X-ray data. DFT calculations show that upon solvation both Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) molecular orbitals are stabilized and their energy gap is increased. TD-DFT calculations show that the intense broad band centered at lambda(max) similar to 506 nm is assigned to "mixed metal-ligand-to-ligand charge-transfer" (MMLLCT) while the weak low energy band centered on similar to 840 nm is assigned to the pure MLCT transition. The low intensity for the low energy MLCT transition can be explained by the large mixing between the azoimine (L) and (Ru(d pi)) orbital. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.04.037

文献信息

• Synthesis and characterization of ruthenium(II) azoimine-diphosphine mixed-ligand complexes
  作者：Mousa Al-Noaimi、Musa I. El-Barghouthi、Mohammad El-khateeb、Obada S. Abdel-Rahman、Helmar Görls、Robert J. Crutchley

  DOI：10.1016/j.poly.2008.05.026

  日期：2008.8

  A novel family of the general type cis-[Ru-II(dppe)LCl2] L=C6H5N=NC(COCH3)=NAr, Ar= 2,4,6-trimethylphenyl(L-1), 2,5-dimethylphenyl(L-2), 4-toly(L-3), phenyl(L-4), 4-methoxyphenyl(L-5), 4-chlorophenyl(L-6), 4-nitrophenyl (L-7), 2,5-dichlorophenyl (L-8); dppe=Ph2P(CH2)(2)PPh2} has been synthesized. These complexes have been characterized through analytical, spectroscopic (IR, UV-Vis, and NMR) and electrochemical (cyclic voltammetry) techniques. In addition, complex 4 (where L = L-4) has been further characterized by X-ray diffraction analysis. Crystallographic, electrochemical and electronic spectral data are all consistent with the azomethine ligands possessing strong pi-acceptor properties. These pi-acceptor properties can be "tuned" by a judicious choice of substituent on the azomethine ligand. (C) 2008 Elsevier Ltd. All rights reserved.
• Ruthenium(II) complex of the novel azoimine ligand, α-acetyl-α-phenylazo-4-chlorophenylazomethine
  作者：Mousa Z. Al-Noaimi、Raid J. Abdel-Jalil、Salim F. Haddad、Rawhi H. Al-Far、Robert J. Crutchley

  DOI：10.1016/j.ica.2006.02.045

  日期：2006.5

  The novel azoimine ligand alpha-acetyl-alpha-phenylazo-4-chlorophenylazomethine (L) was prepared and characterized. Its coordination chemistry to Ru(II) was investigated by the preparation and characterization of the complex trans-[Ru(bpy)LCl2] where bpy is 2,2'-bipyridine. A crystal structure of this complex showed that L is a bidentate ligand and coordinates to Ru(II) by azo-and imine-nitrogen donor atoms. Cyclic voltammetry and spectroelectrochemistry were performed on this complex and the visible region absorption bands assigned. L is shown to be a strong pi-acid ligand. (c) 2006 Elsevier B.V. All rights reserved.
• X-ray structure and DFT study of neutral mixed phosphine azoimine complexes of ruthenium
  作者：Mousa Al-Noaimi、Musa I. El-Barghouthi、Obada S. Abdel-Rahman、Salim F. Haddad、Abdel Monem Rawashdeh

  DOI：10.1016/j.poly.2011.04.037

  日期：2011.6

  Geometry optimization for a cis-[Ru-II(dppe)LCl2] (1-8) L = C6H5N=NC(COCH3)=NAr, Ar = 2,4,6-trimethylphenyl (L-1), 2,5-dimethylphenyl (L-2), 4-tolyl (L-3), phenyl (L-4), 4-methoxyphenyl (L-5), 4-chlorophenyl (L-6) 4-nitrophenyl (L-7), 2,5-dichlorophenyl (L-8); dppe = Ph2P(CH2)(2)PPh2} was effected using the GAUSSIAN 03 protocol at density functional theory (DFT) B3LYP level with 6-31G*/lanl2dz mixed basis. In addition, the complex cis-[Ru-II(dppe)L3Cl2] (3) has been further characterized by X-ray diffraction analysis. It was found that the optimized structure using 6-31G*/lanl2dz has a large agreement with the X-ray data. DFT calculations show that upon solvation both Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) molecular orbitals are stabilized and their energy gap is increased. TD-DFT calculations show that the intense broad band centered at lambda(max) similar to 506 nm is assigned to "mixed metal-ligand-to-ligand charge-transfer" (MMLLCT) while the weak low energy band centered on similar to 840 nm is assigned to the pure MLCT transition. The low intensity for the low energy MLCT transition can be explained by the large mixing between the azoimine (L) and (Ru(d pi)) orbital. (C) 2011 Elsevier Ltd. All rights reserved.