N,N'-bis((diphenylphosphino)methyl)naphthalene-1,5-diamine | 1173405-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-bis((diphenylphosphino)methyl)naphthalene-1,5-diamine
• 英文别名: dpna；1-N,5-N-bis(diphenylphosphanylmethyl)naphthalene-1,5-diamine
• CAS: 1173405-12-3
• 化学式: C₃₆H₃₂N₂P₂
• 分子量: 554.611
• InChiKey: LPCPFRFHPYFMNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (tetrahydrothiophene)gold(I) chloride 、 N,N'-bis((diphenylphosphino)methyl)naphthalene-1,5-diamine 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以40%的产率得到[(N,N'-bis((diphenylphosphino)methyl)naphthalene-1,5-diamine)(AuCl)2]
  参考文献：
  名称：

  Gold(I) Chloride Complexes of Polyphosphine Ligands with Electron-Rich Arene Spacer: Gold–Arene Interactions

  摘要：

  The reactions of Au(tht)Cl (tht = tetrahydrothiophene) with the electron-rich-arene-spacer-containing polyphosphine ligands N,N'-bis((diphenylphosphino)methyl)benzene-1,4-diamine (Dpba), N,N'-bis((diphenylphosphino)methyl)naphthalene-1,5-diamine (Dpna), N,N,N',N'-tetralcis((diphenylphosphino)methyl)benzene-1,4-diamine (Pbaa), N,N,N',N'-tetrakis-((diphenylphosphino)methyl)naphthalene-1,5-diamine (Pnaa), and N,N,N',N'-tetralcis((diphenylphosphino)methyl)biphenyl-4,4'-diamine (Pbbaa) lead to [Dpba(AuCl)2] (1), [Dpna(AuCl)(2)] (2), [Pnaa(AuCl)(4)] (3), [Pbbaa(AuCl)(4) (4). and [Pbaa(AuCl)(4)] (5), which are characterized by H-1 and P-31 NMR, IR, elemental analysis, and X-ray crystal structure analysis. These complexes exhibit weak Au arene interactions with the electron-rich arene spacer, while the Au arene interactions are modified by a combination of electronic and steric effects from the ligands. Different from monomeric complexes 1, 2, 3, and 4, complex 5 in the solid state exhibits a centrosymmetric trimeric unit that is constructed by intermolecular Au center dot center dot center dot Au interactions between the central molecule and the two symmetry-related terminal molecules and in which the conformation of the central molecule is different from that of the two symmetric terminal molecules. On the basis of the Kochi's geometric criteria and the crystal structural parameters relating to Au-arene interactions, the Au center dot center dot center dot C-arene contacts in 3 and 4 feature nearly eta(2)-arene interactions, while the Au center dot center dot center dot C-arene contacts in 5 can be described as eta(1)-arene interactions, and the Au center dot center dot center dot C-arene contacts in 1 and 2, are very weak due to intermolecular N-H center dot center dot center dot Cl interactions.

  DOI：

  10.1021/om201276w

文献信息

• Synthesis, structures and characterization of a series of Cu(i)-diimine complexes with labile N,N′-bis((diphenylphosphino)methyl)naphthalene-1,5-diamine: diverse structures directed by π–π stacking interactions
  作者：Qing-Ling Ni、Xuan-Feng Jiang、Liu-Cheng Gui、Xiu-Jian Wang、Kun-Guo Yang、Xian-Shu Bi

  DOI：10.1039/c1nj20355j

  日期：——

  Five complexes [Cu2(phen)2(dpna)](ClO4)2 (1), [Cu2(dmp)2(dpna)](ClO4)2 (2), [Cu(phen)(dpna)](ClO4)}n (3), [Cu2(pz)(dpna)](ClO4)2 (4) and [Cu2(pz)(dpna)2](ClO4)2 (5) (phen = 1,10-phenanthroline, dmp = 2,9-dimethyl-1,10-phenanthroline, pz = pyrazine, dpna = N,N′-bis((diphenylphosphino)methyl)naphthalene-1,5-diamine) were rationally synthesized and characterized by elemental analysis, IR, MS and X-ray

  五种络合物[Cu 2（phen）2（dpna）]（ClO 4）2（1），[Cu 2（dmp）2（dpna）]（ClO 4）2（2），[Cu（phen）（dpna ）]（ClO 4）} n（3），[Cu 2（pz）（dpna）]（ClO 4）2（4）和[Cu 2（pz）（dpna）2 ]（ClO 4）2（5） （phen =1,10-菲咯啉，dmp = 2,9-二甲基-1,10-菲咯啉，pz = 吡嗪，dpna = N，N'-双（（二苯基膦基）甲基）萘-1,5-二胺经元素分析，IR，MS和X射线衍射分析合理合成并表征。这些结构的构建是基于π系统的电子互补性，通过贫电子的二亚胺环与富电子的萘环之间的分子内π-π堆积相互作用来指导的，而dpna的不稳定性可以满足其构象的需求。在1，2和3，DPNA取反式协调模式，以桥接两个铜+。图1和图2是具有三层π堆积构型的离散的双核络合物，其中富电子的萘环
• Gold(I) Chloride Complexes of Polyphosphine Ligands with Electron-Rich Arene Spacer: Gold–Arene Interactions
  作者：Qing-Ling Ni、Xuan-Feng Jiang、Ting-Hong Huang、Xiu-Jian Wang、Liu-Cheng Gui、Kun-Guo Yang

  DOI：10.1021/om201276w

  日期：2012.3.26

  The reactions of Au(tht)Cl (tht = tetrahydrothiophene) with the electron-rich-arene-spacer-containing polyphosphine ligands N,N'-bis((diphenylphosphino)methyl)benzene-1,4-diamine (Dpba), N,N'-bis((diphenylphosphino)methyl)naphthalene-1,5-diamine (Dpna), N,N,N',N'-tetralcis((diphenylphosphino)methyl)benzene-1,4-diamine (Pbaa), N,N,N',N'-tetrakis-((diphenylphosphino)methyl)naphthalene-1,5-diamine (Pnaa), and N,N,N',N'-tetralcis((diphenylphosphino)methyl)biphenyl-4,4'-diamine (Pbbaa) lead to [Dpba(AuCl)2] (1), [Dpna(AuCl)(2)] (2), [Pnaa(AuCl)(4)] (3), [Pbbaa(AuCl)(4) (4). and [Pbaa(AuCl)(4)] (5), which are characterized by H-1 and P-31 NMR, IR, elemental analysis, and X-ray crystal structure analysis. These complexes exhibit weak Au arene interactions with the electron-rich arene spacer, while the Au arene interactions are modified by a combination of electronic and steric effects from the ligands. Different from monomeric complexes 1, 2, 3, and 4, complex 5 in the solid state exhibits a centrosymmetric trimeric unit that is constructed by intermolecular Au center dot center dot center dot Au interactions between the central molecule and the two symmetry-related terminal molecules and in which the conformation of the central molecule is different from that of the two symmetric terminal molecules. On the basis of the Kochi's geometric criteria and the crystal structural parameters relating to Au-arene interactions, the Au center dot center dot center dot C-arene contacts in 3 and 4 feature nearly eta(2)-arene interactions, while the Au center dot center dot center dot C-arene contacts in 5 can be described as eta(1)-arene interactions, and the Au center dot center dot center dot C-arene contacts in 1 and 2, are very weak due to intermolecular N-H center dot center dot center dot Cl interactions.