2,3-dichloro-5,6-dicyano-4-hydroxyphenolate | 46257-45-8

• 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: 2,3-dichloro-5,6-dicyano-4-hydroxyphenolate
• CAS: 46257-45-8
• 化学式: C₈HCl₂N₂O₂
• 分子量: 228.014
• InChiKey: QNDGAROPZNKYNK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-二氯-5,6-二氰基-1,4-苯醌 以 二甲基亚砜 为溶剂， 生成 2,3-dichloro-5,6-dicyano-4-hydroxyphenolate
  参考文献：
  名称：

  Free energy hydride affinities of quinones in dimethyl sulfoxide solution

  摘要：

  Free energy hydride affinities in solution defined by reaction i [(i) Q(s) + H-s reversible (QH-)s, DELTAG(hydride)(Q)s] were evaluated for a number of quinones (Q) in dimethyl sulfoxide solution using reaction ii [(ii) -DELTAG(hydride)(Q)s = 2.303RTpK(a)(QH-)s + FDELTAE-degrees(NHE)[(Q.-/Q2-)s + (Q/Q.-)s] + C] derived from a thermochemical cycle. The constant C corresponds to -FE-degrees(NHE)[(H+/H.)s + (H./H-)s] which is equal to 69.9 kcal/mol in dimethyl sulfoxide. The pK(a) of hydroquinone monoanions (QH-) were determined by the overlapping indicator method. Reversible electrode potentials for both the first and second charge transfers to Q were determined by cyclic voltammetry. Values of DELTAG(hydride)(Q)DMSO ranging from -58 to -101 kcal/mol were observed. Hydride affinities of substituted benzoquinones (BQ) were found to be linearly correlated with the corresponding electron affinities in solution. Equilibrium constants for the reactions of BQ with the NADH model compound 10-methylacridan were estimated, and the thermochemical results are discussed in terms of the one- and the two-step mechanisms of hydride-transfer reactions.

  DOI：

  10.1021/jo00071a011

文献信息

• Na⁺-Catalyzed Reduction of Semiquinone Radical Anions by NADH Analogues
  作者：Shunichi Fukuzumi、Yoshihiro Tokuda

  DOI：10.1246/cl.1992.1497

  日期：1992.8

  Stable radical anions such as p-chloranil radical anion (Cl4Q−•) are reduced by NADH analogues, 1-benzyl-1,4-dihydronicotinamide (BNAH) and 10-methyl-9,10-dihydroacridine (AcrH2), to yield the corresponding hydroquinone anions. The addition of NaClO4 to the BNAH-Cl4Q−• system results in a significant increase in the rate of the one-electron reduction of Cl4Q−•, while no acceleration effect has been

  NADH 类似物、1-苄基-1,4-二氢烟酰胺 (BNAH) 和 10-甲基-9,10-二氢吖啶 (AcrH2) 可还原对氯苯醌自由基阴离子 (Cl4Q−•) 等稳定的自由基阴离子，从而生成相应的氢醌阴离子。将 NaClO4 添加到 BNAH-Cl4Q-• 系统导致 Cl4Q-• 的单电子还原速率显着增加，而通过添加 Bu4NClO4 没有观察到加速效果。