pentacyanophenol

• 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: pentacyanophenol
• 英文别名: Pentacyano phenol；6-hydroxybenzene-1,2,3,4,5-pentacarbonitrile
• 化学式: C₁₁HN₅O
• 分子量: 219.162
• InChiKey: XBYJYGFMGMNUDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 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：
  139
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 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

• Anhydrous flouride salts and reagents and methods for their production
  申请人：DiMagno G. Stephen

  公开号：US20060089514A1

  公开（公告）日：2006-04-27

  Anhydrous organic fluoride salts and reagents prepared by a method comprising the nucleophilic substitution of a fluorinated aromatic or fluorinated unsaturated organic compound with a salt having the formula: [Q n M] x+ A x − in an inert polar, aprotic solvent; wherein M is an atom capable of supporting a formal positive charge, the n groups Q are independently varied organic moieties, n is an integer such that the [Q n M] carries at least one formal positive charge, x is an integer defining the number of formal positive charge(s), +, carried by the [Q n M], A − is an anionic nucleophile capable of substituting for F in the fluorinated compound and F represents fluorine or a radioisotope thereof.

  由一种方法制备的无水有机氟化物盐和试剂，该方法包括用具有以下公式的盐进行氟化芳香族或氟化不饱和有机化合物的亲核取代：[QnM]x+Ax−，其中M是能够支持正式正电荷的原子，n个Q基团是独立变化的有机基团，n是一个整数，使得[QnM]至少带有一个正式正电荷，x是定义由[QnM]携带的正式正电荷数的整数，+，A−是能够取代氟化合物中F的阴离子亲核试剂，F代表氟或其同位素。
• US7592486B2
  申请人：——

  公开号：US7592486B2

  公开（公告）日：2009-09-22
• 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.