4-chloro-2,3,5,6-tetracyanophenol

• 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: 4-chloro-2,3,5,6-tetracyanophenol
• 英文别名: 3-Chloro-6-hydroxybenzene-1,2,4,5-tetracarbonitrile
• 化学式: C₁₀HClN₄O
• 分子量: 228.597
• InChiKey: GWTXUQOXZPZIEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 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：
  115
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-chloro-2,3,5,6-tetracyanophenol 在 吡啶 、 三氯氧磷 作用下， 反应 0.12h， 以0.8 mg的产率得到3,6-dichloro-benzene-1,2,4,5-tetracarbonitrile
  参考文献：
  名称：

  Successive Photosubstitution of Hexachlorobenzene with Cyanide Ion

  摘要：

  We report a novel nucleophilic polysubstitution reaction of hexachlorobenzene (HCB) with cyanide ion in acetonitrile/water. Successive photocyanations of HCB occur with high quantum yield (phi(diss) --> 0.18) without the need for an electron acceptor, to give as products pentacyanophenol, 4-chloro-2,3,5,6-tetracyanophenol, and a dichlorotricyanophenol. The phenol functional group is introduced by competing hydrolysis of the polycyanochlorinated benzenes. Sensitization and quenching experiments indicate a triplet reactive excited state. Variation of [CN-] at constant [HCB] follows the expected relationship phi(diss) -1 proportional to [CN-](-1), but variation of [HCB] at constant [CN-] shows that the reaction becomes less efficient with increasing [HCB], consistent with the formation of an unproductive excimer.

  DOI：

  10.1021/ja980403n
• 作为产物：
  描述：

  六氯苯 、 氰化钠 在 水 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 4-chloro-2,3,5,6-tetracyanophenol 、 pentacyanophenol
  参考文献：
  名称：

  Successive Photosubstitution of Hexachlorobenzene with Cyanide Ion

  摘要：

  We report a novel nucleophilic polysubstitution reaction of hexachlorobenzene (HCB) with cyanide ion in acetonitrile/water. Successive photocyanations of HCB occur with high quantum yield (phi(diss) --> 0.18) without the need for an electron acceptor, to give as products pentacyanophenol, 4-chloro-2,3,5,6-tetracyanophenol, and a dichlorotricyanophenol. The phenol functional group is introduced by competing hydrolysis of the polycyanochlorinated benzenes. Sensitization and quenching experiments indicate a triplet reactive excited state. Variation of [CN-] at constant [HCB] follows the expected relationship phi(diss) -1 proportional to [CN-](-1), but variation of [HCB] at constant [CN-] shows that the reaction becomes less efficient with increasing [HCB], consistent with the formation of an unproductive excimer.

  DOI：

  10.1021/ja980403n

文献信息

• Successive Photosubstitution of Hexachlorobenzene with Cyanide Ion
  作者：Alexandre Konstantinov、Carol A. Kingsmill、George Ferguson、Nigel J. Bunce

  DOI：10.1021/ja980403n

  日期：1998.6.1

  We report a novel nucleophilic polysubstitution reaction of hexachlorobenzene (HCB) with cyanide ion in acetonitrile/water. Successive photocyanations of HCB occur with high quantum yield (phi(diss) --> 0.18) without the need for an electron acceptor, to give as products pentacyanophenol, 4-chloro-2,3,5,6-tetracyanophenol, and a dichlorotricyanophenol. The phenol functional group is introduced by competing hydrolysis of the polycyanochlorinated benzenes. Sensitization and quenching experiments indicate a triplet reactive excited state. Variation of [CN-] at constant [HCB] follows the expected relationship phi(diss) -1 proportional to [CN-](-1), but variation of [HCB] at constant [CN-] shows that the reaction becomes less efficient with increasing [HCB], consistent with the formation of an unproductive excimer.