ethidium nitrate | 151901-99-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethidium nitrate
• CAS: 151901-99-4
• 化学式: C₂₁H₂₀N₃*NO₃
• 分子量: 376.415
• InChiKey: JFKXAHCSHIFBIA-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  122.12
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethidium nitrate 在 AgNO₃ 、 NH₄Cl 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 cis-{diamminechloro(N3-ethidium)platinum(II)} chloride*2.5H2O
  参考文献：
  名称：

  Synthesis, characterization, DNA binding properties, and solution thermochromism of platinum(II) complexes of the ethidium cation: regiospecificity in a DNA-promoted reaction

  摘要：

  The reaction of [Pt(NH3).Cl4-n](n-2) (n = 1, 2, and 3) complexes with 1 equiv of the ethidium (Etd) cation afforded cis-[Pt(NH3)2(Etd)Cl]2+, trans-[Pt(NH3)2(Etd)Cl]2+, cis-[Pt(NH3)(Etd)Cl2]+, and [Pt(NH3)3(Etd)]3+, in which Etd is coordinated to platinum through one of its two exocyclic amino groups. These N3 and N8 linkage isomers were separated by reverse-phase HPLC. The platinum coordination sites on ethidium were determined with the use of both Pt-195 and H-1 NMR spectroscopy as well as by single-crystal X-ray diffraction studies of the N3 and N8 isomers of cis-[Pt(NH3)2(Etd)Cl]Cl2. Solutions of the acetate salts of all the complexes displayed temperature-dependent optical spectroscopic changes in which a transition at approximately 490 nm (orange) diminished in intensity with concomitant growth of a band at approximately 640 nm (blue) as the temperature increased. This reversible thermochromic phenomenon was shown to arise from proton transfer between the coordinated exocyclic amino group and the acetate counterion. Temperature-dependent electronic spectral changes resulting from this reaction were fit to the appropriate equilibrium expressions by global analysis, yielding the corresponding thermodynamic parameters, and DELTAS-degrees. Acidity constants for the deprotonation of the coordinated exocyclic amino groups were determined from such equilibrium studies of most of the complexes in methanol and converted to the corresponding values in aqueous solution. These experiments revealed the effects of overall charge, linkage isomerism, and platinum geometric isomerism on the pK(a) values of the coordinated amino group. Through a Fenske-Hall molecular orbital analysis, the 490-nm band was assigned as a charge-transfer transition from the lone pair orbital of the uncoordinated exocyclic amino nitrogen to the pi* orbital (LUMO) of the phenanthridinium ring. The blue band at approximately 640 nm was best described as a charge-transfer transition from a pi orbital delocalized over the Pt-N(coordinated exocyclicamine) linkage to the pi* orbital of the phenanthridinium ring. The ability to assign the relative pK(a) values of the linkage isomers has been used to demonstrate that the previously reported DNA-promoted reaction between cis-DDP and ethidium is regiospecific, with the platinum reacting primarily at the N8 position of the Etd ring.

  DOI：

  10.1021/ja00077a037