1,10-phenanthroline-5,6-diol hydrochloride | 85565-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 1,10-phenanthroline-5,6-diol hydrochloride
• CAS: 85565-50-0
• 化学式: C₁₂H₈N₂O₂*ClH
• 分子量: 248.669
• InChiKey: BWMXVZVHJRWJEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.24
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-苄基-2-氯-N-甲基乙酰胺 、 1,10-phenanthroline-5,6-diol hydrochloride 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以80%的产率得到1,10-phenanthroline-5,6-bis(N-methyl-N-benzyl-1'-oxopropylamide)
  参考文献：
  名称：

  Terminal group effects on the fluorescence spectra of Eu(III) nitrate complexes with a family of amide-based 1,10-phenanthroline derivatives

  摘要：

  Four ligands 1,10-phenanthroline-5,6-bis(N,N-dibenzyl-l'-oxopropylamide) (L-a) 1,10-phenanthroline-5,6-bis(N-methyl-N-benzyl-l'oxopropylamide) (L-b) 1,10-phenanthroline-5,6-bis(N-benzyl-l'-oxopropylamide) (L-c) and 1,10-phenanthroline-5,6-bis(N,N-diethyl-l'oxopropylamide) (L-d), and their lanthanide(III) (La and Eu) complexes were synthesized. The complexes were characterized by elemental analysis, IR, fluorescence spectroscopy and conductivity. The lanthanide atoms are coordinated by O atoms from C=O, Ar-O-C and N atoms from phen With the difference of the ligands, the fluorescent intensities of the Eu(Ill) complexes vary regularly in the THF solution. Some factors that influence the fluorescent intensity were discussed. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2005.03.010
• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 在 盐酸肼 作用下， 反应 0.17h， 生成 1,10-phenanthroline-5,6-diol hydrochloride
  参考文献：
  名称：

  新型euro和ter多核配合物与酰胺基1,10-菲咯啉衍生物的合成，红外光谱和荧光光谱。

  摘要：

  合成了酰胺基的1,10-菲咯啉（phen）衍生物及其与euro（III）和b（III）离子的配合物。通过元素分析，红外光谱和电导率对配合物进行表征。O和ter离子由C = O的O原子，Ar-OC和phen的N原子配位。研究了配合物在THF，二恶烷，MeCN和DMF中的荧光性质。在紫外光的激发下，这些络合物表现出characteristic和ter离子的特征荧光。讨论了影响荧光强度的溶剂因素。

  DOI：

  10.1016/j.saa.2003.09.009

文献信息

• 5,6-Dihydroxy-1,10-phenanthrolinium-1,10-ium dichloride
  作者：Waynie Olaprath、Kraig A. Wheeler、Mark E. McGuire

  DOI：10.1007/s10870-011-0003-0

  日期：2011.6

  5,6-Dihydroxy-1,10-phenanthroline, obtained from recrystallization of a side-product of a condensation reaction between 1,10-phenanthroline-5,6-dione and 5,6-diamino-1,3-dimethyluracil, has been isolated as a dihydrochloride (C12H8N2O2·2HCl·0.5CH3CN) by vapor diffusion of acetonitrile into an ethanol/HCl solution. The compound crystallizes in the triclinic space group $$ P\overline1} $$ with a = 5.8334(1) Å, b = 9.8041(2) Å, c = 11.9895(2) Å, α = 81.511(1)°, β = 76.395(1)°, γ = 81.429(1)°, and V = 654.48(2) Å3, Z = 2, R[F 2 > 2σ(F 2)] = 0.028, and wR(F 2) = 0.078. The crystal packing is stabilized by two N–H+···Cl− interactions (2.18(3) Å, 2.13(2) Å) and two O–H···Cl− interactions (2.11(3) Å, 2.20(3) Å). Pi-stacking of the phenanthrolinium rings results in an interplanar distance of 3.431(5) Å with the phenanthrolinium ring centroids displaced from each other by ~6 Å. The results for this diprotonated species are compared to those reported by Lin et al. (Acta Cryst E65:o2367, 2009) for the monoprotonated form and this reveals the possibility of using the relative –OH/phenanthroline ring orientations as a qualitative diagnostic of metal–ligand interactions in metal complexes of this ligand (Larsson and Ohrstrom in Inorg Chim Acta 357:657, 2004; Guan et al. in Acta Cryst C64:m311, 2008). The crystal structure of the diprotonated form of 5,6-dihdroxy-1,10-phenanthroline (5,6-dihydroxy-1,10-phenanthrolinium-1,10-ium dichloride) is discussed and compared to both the monoprotonated form and those complexed with Mn(II) and Co(III) reported in the literature.

  5,6- 二羟基-1,10-菲罗啉是 1,10-菲罗啉-5,6-二酮和 5,6- 二氨基-1,3-二甲基脲嘧啶缩合反应的副产物，通过乙腈蒸发扩散到乙醇/HCl 溶液中分离出二盐酸盐 (C12H8N2O2-2HCl-0.5CH3CN)。该化合物在三linic 空间群 $$ P\overline1} $$ 中结晶，a = 5.8334(1) 埃，b = 9.8041(2) 埃，c = 11.9895(2) 埃，α = 81.511(1)°，β = 76.395(1)°，γ = 81.429(1)°，V = 654.48(2) Å3，Z = 2，R[F 2 > 2σ(F 2)] = 0.028，wR(F 2) = 0.078。两种 N-H+-Cl- 相互作用（2.18(3) 埃、2.13(2) 埃）和两种 O-H-Cl- 相互作用（2.11(3) 埃、2.20(3) 埃）稳定了晶体堆积。菲罗啉环的π-堆积导致平面间距为 3.431(5) 埃，菲罗啉环的中心点彼此相距约 6 埃。该双质子化物种的结果与 Lin 等人（Acta Cryst E65:o2367, 2009）报告的单质子化形式的结果进行了比较，从而揭示了使用 -OH/ 菲罗啉环的相对取向作为该配体的金属配合物中金属-配体相互作用的定性诊断的可能性（Larsson 和 Ohrstrom，发表于 Inorg Chim Acta 357:657, 2004；Guan 等人，发表于 Acta Cryst C64:m311, 2008）。本文讨论了 5,6-二羟基-1,10-菲罗啉的二质子化形式（5,6-二羟基-1,10-菲罗啉鎓-1,10-二氯化物）的晶体结构，并将其与文献中报道的单质子化形式以及与锰（II）和钴（III）络合的形式进行了比较。
• Chemical properties of phenanthrolinequinones and the mechanism of amine oxidation by o-quinones of medium redox potentials
  作者：Timothy S. Eckert、Thomas C. Bruice

  DOI：10.1021/ja00351a049

  日期：1983.6