| 53715-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• CAS: 53715-59-6
• 化学式: C₅H₃ClN
• 分子量: 112.539
• InChiKey: SJGNPEZYXVEDED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  、 2-巯基嘧啶 在 4,4'-联吡啶 、 potassium tert-butylate 作用下， 以 氨 为溶剂， 生成 2-(5-Chloropyridin-2-yl)sulfanylpyrimidine
  参考文献：
  名称：

  Is Selective Monosubstitution of Dihalides via SRN1 Reaction Feasible? An Electrochemical Approach for Dichloroarenes

  摘要：

  1,4-Dichlorobenzene and dichloropyridines undergo S(RN)1 reactions with various nucleophiles upon electrochemical initiation. Substitution can compete with reduction only when indirect electrolyses at low current are performed. Selective formation of monosubstitution products is observed when the nucleophiles used behave as electron-donating groups when attached to the aromatic moiety, a situation which is just the opposite of what had been observed when the same reactions were initiated photochemically. This surprising difference in behavior can be rationalized in terms of different capabilities of both activation methods to generate the key monosubstitution anion radical, ArNuX(.-). Kinetic and thermodynamic data concerning the reactivity of dichloroarenes in such processes are presented and discussed.

  DOI：

  10.1021/jo00106a009
• 作为产物：
  描述：

  2,5-二氯吡啶 以 氨 为溶剂， 生成 、 (2-chloropyridine-5-yl)1,28g-Biphenylmethylamine
  参考文献：
  名称：

  Is Selective Monosubstitution of Dihalides via SRN1 Reaction Feasible? An Electrochemical Approach for Dichloroarenes

  摘要：

  1,4-Dichlorobenzene and dichloropyridines undergo S(RN)1 reactions with various nucleophiles upon electrochemical initiation. Substitution can compete with reduction only when indirect electrolyses at low current are performed. Selective formation of monosubstitution products is observed when the nucleophiles used behave as electron-donating groups when attached to the aromatic moiety, a situation which is just the opposite of what had been observed when the same reactions were initiated photochemically. This surprising difference in behavior can be rationalized in terms of different capabilities of both activation methods to generate the key monosubstitution anion radical, ArNuX(.-). Kinetic and thermodynamic data concerning the reactivity of dichloroarenes in such processes are presented and discussed.

  DOI：

  10.1021/jo00106a009

文献信息

• Is Selective Monosubstitution of Dihalides via SRN1 Reaction Feasible? An Electrochemical Approach for Dichloroarenes
  作者：Christian Amatore、Catherine Combellas、Nour-Eddine Lebbar、Andre Thiebault、Jean-Noeel Verpeaux

  DOI：10.1021/jo00106a009

  日期：1995.1

  1,4-Dichlorobenzene and dichloropyridines undergo S(RN)1 reactions with various nucleophiles upon electrochemical initiation. Substitution can compete with reduction only when indirect electrolyses at low current are performed. Selective formation of monosubstitution products is observed when the nucleophiles used behave as electron-donating groups when attached to the aromatic moiety, a situation which is just the opposite of what had been observed when the same reactions were initiated photochemically. This surprising difference in behavior can be rationalized in terms of different capabilities of both activation methods to generate the key monosubstitution anion radical, ArNuX(.-). Kinetic and thermodynamic data concerning the reactivity of dichloroarenes in such processes are presented and discussed.