N,N'-dicyano-4-4'-diaminobiphenyl | 84425-40-1

• 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: N,N'-dicyano-4-4'-diaminobiphenyl
• 英文别名: N,N-dicyano-4,4'-diaminobiphenyl；4,4′-dicyanamidobiphenyl；4,4'-dicyanamidobiphenyl；[4-[4-(Cyanoamino)phenyl]phenyl]cyanamide
• CAS: 84425-40-1
• 化学式: C₁₄H₁₀N₄
• 分子量: 234.26
• InChiKey: OEHUKUCNBVFUEO-UHFFFAOYSA-N

物化性质

• 沸点：
  395.3±52.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-dicyano-4-4'-diaminobiphenyl 、 chloroauric acid 以 乙醇 、 水 为溶剂， 反应 15.0h， 以95%的产率得到
  参考文献：
  名称：

  Sonochemical synthesis of Au nanowires in the III–I oxidation state bridged by 4,4′-dicyanamidobiphenyl and their application as selective CO gas sensors

  摘要：

  使用bpH2合成了Au纳米线，用于制作具有高灵敏度的CO气体传感器，在室温下使用。

  DOI：

  10.1039/c4dt03427a
• 作为产物：
  描述：

  1-异氰酸-4-(4-异氰酸苯基)苯 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以98%的产率得到N,N'-dicyano-4-4'-diaminobiphenyl
  参考文献：
  名称：

  Sodium Bis(trimethylsilyl)amide in the ‘One-Flask’ Transformation of ­Isocyanates to Cyanamides

  摘要：

  在室温下的四氢呋喃中，使用双（三甲基硅）酰胺钠作为脱氧剂，通过 "单瓶 "反应从异氰酸酯中成功制备了氰化物。

  DOI：

  10.1055/s-2006-932470

文献信息

• A pentaammineruthenium(III) dimer with the novel bridging ligand 4,4′-dicyanamidobiphenyl dianion
  作者：Christopher A. White、Corinne Bensimon、Robert J. Crutchley、Manuel A.S. Aquino、J.E. Greedan

  DOI：10.1139/v96-247

  日期：1996.11.1

  The novel ligand 4,4′-dicyanamidobiphenyl dianion (bp²⁻) has been synthesized and characterized by ¹³C NMR spectroscopy, cyclic voltammetry, and crystallography. The crystal structure of [Ph₄As]₂[bp]•H₂O showed that bp²⁻ is approximately planar with a dihedral angle of 8.2° between phenyl ring planes and the cyanamide groups in an anti conformation. The water of crystallization is asymmetrically hydrogen bonded between cyanamide groups of adjacent bp²⁻ ions. The crystal data for C₆₂H₄₈N₄As₂ + H₂O are monoclinic crystal system and space group P2₁/c with a = 12.998(5) Å, b = 13.465(4) Å, c = 28.703(13) Å, β = 98.94(3)°, V = 4963(3) ų and Z = 4. The structure was refined by using 4555 reflections with I > 2.5σ(I) to an R factor of 0.058. The complex, [(NH₃)₅Ru)₂(μ-bp)][X]₄, where X = tosylate or PF₆⁻ ions, was also synthesized and characterized by ¹H NMR spectroscopy, cyclic voltammetry, spectroelectrochemistry, and temperature-dependent magnetic susceptibility measurements. From cyclic voltammetry measurements, the comproportionation constants to form the mixed-valence complex [(NH₃)₅Ru)₂(μ-bp)]³⁺ were estimated to be 4.1, 16, and 22 in water, acetonitrile, and nitromethane, respectively. The trend and magnitude of K_c suggests solvent valence trapping of a weakly coupled Class II ion. The MMCT band of the mixed-valence complex had to be deconvoluted from the low-energy LMCT band and had the following properties in acetonitrile, ν_max = 8400 cm⁻¹, ε_max = 3300 M⁻¹ cm⁻¹, and Δν_1/2 = 3300 cm⁻¹. The weak superexchange mediating properties of bp²⁻ compared to 1,4-dicyanamidobenzene dianion were suggested to arise from the larger barrier to the formation of the radical anion bp⁻. Key words: cyanamido, mixed valence, superexchange, ruthenium.

  新型配体4,4'-二氰胺基联苯二阴离子（bp^2−）已经通过^13C核磁共振光谱、循环伏安法和晶体学合成并表征。[Ph_4As]_2[bp]•H_2O的晶体结构显示，bp^2−近似平面，苯环平面与氰胺基之间的二面角为8.2°，呈反式构象。结晶水以不对称氢键形式存在于相邻bp^2−离子的氰胺基之间。C_62H_48N_4As_2 + H_2O的晶体数据为单斜晶系，空间群为P2_1/c，a = 12.998(5) Å，b = 13.465(4) Å，c = 28.703(13) Å，β = 98.94(3)°，V = 4963(3) Å^3，Z = 4。该结构经过4555个I ＞ 2.5σ(I)的衍射反射进行了细化，R因子为0.058。复合物[(NH_3)_5Ru)_2(μ-bp)][X]_4，其中X = 对甲苯磺酸盐或PF_6^−离子，也通过^1H核磁共振光谱、循环伏安法、光电化学和温度相关磁化率测量进行了合成和表征。通过循环伏安法测量，形成混合价态复合物[(NH_3)_5Ru)_2(μ-bp)]^3+的复合常数在水、乙腈和硝基甲烷中分别估计为4.1、16和22。K_c的趋势和大小表明溶剂价态俘获了弱耦合的II类离子。混合价态复合物的MMCT带必须从低能LMCT带中解离，并在乙腈中具有以下性质，ν_max = 8400 cm^−1，ε_max = 3300 M^−1 cm^−1，Δν_1/2 = 3300 cm^−1。与1,4-二氰胺基苯二阴离子相比，bp^2−的弱超交换介导性质被认为是由于形成自由基阴离子bp^−的较大障碍。关键词：氰胺基，混合价态，超交换，钌。
• Synthetic, spectral, electrochemical and structural aspects of some Ru(II) arene complexes with some novel bridging ligands
  作者：P Valerga、M.C Puerta、D.S Pandey

  DOI：10.1016/s0022-328x(01)01446-2

  日期：2002.4

  Reactions of chloro-bridged dimeric Ru(II) complexes [Ru(η6-arene)Cl2}2] with bridging ligands 1,4-dicyanamidobenzene, N,N′-dicyano 4-4′-diaminobiphenyl, 2,5-dichloro-1,4-dicyanamidobenzene and 2,5-dimethyl-1,4-dicyanamidobenzene (referred hereafter as dcdH2, bpH2, ddcl and dmcd) in dicloromethane at room temperature gave binuclear complexes with the general formulation [Ru(η6-arene)Cl2}2(μ-L)].

  的反应氯桥二聚的Ru（II）配合物[茹（η 6 -arene）氯2 } 2 ]与桥连配体的1,4- dicyanamidobenzene，Ñ，Ñ '-dicyano 4-4'-二氨基联苯，2,5-二氯-1,4- dicyanamidobenzene和2,5-二甲基-1,4- dicyanamidobenzene（以下简称dcdH 2，BPH 2在室温下在dicloromethane，DDCL和DMCD），得到双核络合物与一般的制剂[茹（ η 6 -arene）氯2 } 2（μ-L）]。然而，随着这些配合物的配体桥接的反应的[Ru（η 6 -arene）（P）氯2 ]（η 6 -arene =苯或p -cymene; P = PPH 3， PET 3或MePPr我2）在甲醇，在NH存在4 PF 6，得到阳离子芳烃络合物[茹（η 6 -arene）（P）氯} 2（L）] 2+（L = dcdH
• Silver nanoparticles with 4,4′-dicyanamidobiphenyl ligand: Synthesis, photoluminescent and electroluminescent properties and DFT calculations
  作者：Hossein Chiniforoshan、Sara Bahmanpour Khalesi、Leila Tabrizi、Abdol R. Hajipour、Alireza Najafi Chermahini、Morteza Karimzadeh

  DOI：10.1016/j.molstruc.2014.11.011

  日期：2015.2

  In this research, a new complex of 4,4'-dicyanamidobiphenyl (bpH(2)) ligand, Ag(bpH) has been synthesized and characterized by FT-IR, UV-Vis spectroscopies, and elemental analysis. The morphology and size of complex were determined by the scanning electron microscopy (SEM) image. The diameter of the complex was about 61 nm and the nanoparticles were spherical. TGA result indicated that this complex was thermally stable. Also, photoluminescent and electroluminescent properties of Ag(bpH) were reported. The blue-green light emission was observed by fabricating double-layer devices using Ag(bpH) as electron-transport and NPB as hole-transport material. In addition, this complex was optimized by B3LYP/LANL2DZ method. The calculated FT-IR and UV-Vis data are in better agreement with the experimental results. In addition to DFT calculations, natural bond orbital (NBO) was also performed at the same level of theory. (C) 2014 Elsevier B.V. All rights reserved.
• Cytotoxicity and antimicrobial activity of triorganotin(IV) complexes of phenylcyanamide prepared by sonochemical synthesis
  作者：Leila Tabrizi、Patrick McArdle、Andrea Erxleben、Hossein Chiniforoshan

  DOI：10.1016/j.ica.2015.09.011

  日期：2015.11

  This article describes the synthesis and characterization of novel triorganotin(IV) complexes and their potential medicinal applications. Triorganotin(IV) complexes with formulas [(SnMe3)(2)(mu-bp)(H2O)(2)], 1, and [(SnMe3)(4-NO(2)pcyd)], 2, (Me: methyl, bpH(2): 4,4'-dicyanamidobiphenyl and 4-NO(2)pcyd: 4-nitrophenylcyanamide) have been synthesized via a sonochemical process and characterized using multinuclear NMR (H-1, C-13 and Sn-119), Mossbauer spectroscopy, elemental analysis, scanning electron microscopy (SEM) and transmission electron microscopy (TEM). Compounds 1 and 2 were evaluated for their DNA/protein binding with calf thymus DNA (CT-DNA) and bovine serum albumin (BSA), respectively. The in vitro cytotoxicity of 1 and 2 was examined against A549, Du145, HeLa and MCF-7 cancer cell lines. For 1, a promising growth inhibitory effect against HeLa cells was observed that is slightly higher than that of cisplatin. Moreover, the antimicrobial activity of 1 and 2 against different strains of pathogenic bacteria and fungi were tested. The free radical scavenging ability (OH, NO) of 1 and 2 was assessed. (C) 2015 Elsevier B.V. All rights reserved.