1-phenyl-1H-tetrazole-5-thio radical | 82211-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-phenyl-1H-tetrazole-5-thio radical
• CAS: 82211-12-9
• 化学式: C₇H₅N₄S
• 分子量: 177.209
• InChiKey: UVVZUFGMOPAEMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-1H-tetrazole-5-thio radical 、 天然橡胶 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Laser-flash photolysis study of dithiobis (tetrazole); reactivities of tetrazole-thio radical

  摘要：

  The photo-cleavage of S-S bond of 5,5'-dithiobis (1-phenyl-1 H-tetrazole) has been studied by the nanosecond-laser flash photolysis method. The transient absorption band at ca. 430 nm was attributed to 1-phenyl-1 H-tetrazole-5-thio radical forming by the S-S bond fission. For the reaction with conjugated dienes, an addition reaction takes place forming the S-C bond, suggesting that unpaired electron of the radical localizes mainly on the S-atom From the decay rates of the radical, the addition reaction rate constant for 2-methyl-1,3-butadiene is evaluated to be 5.5 x 10(9) M(-1) s(-1) in THF at 23 degrees C, which is as fast as diffusion controlled limit. The reactivity of the radical is ca. 100 times higher than that of the PhS(.). The reactivity of the thio radical to O-2 was too low to evaluate, which is one of the characteristics of a S-centered radical. The rate constant for 1.4-cyclohexadienene (1.4 x 10(8) M(-1) s(-1)) is larger than that of cyclohexene (2.8 x 10(7) M(-1) s(-1)), suggesting the hydrogen abstraction is a main reaction. The MO calculations have been pe:formed for these radicals to reveal the reason of the high reactivity of the radical. (C) 1996 John Wiley & Sons, Inc.

  DOI：

  10.1002/(sici)1097-4601(1996)28:6<405::aid-kin2>3.0.co;2-z
• 作为产物：
  描述：

  5,5′-二硫双(1-苯基-1H-四唑) 生成 1-phenyl-1H-tetrazole-5-thio radical
  参考文献：
  名称：

  搜索自由基对双键的高反应性和低选择性：四唑衍生的噻吩基自由基的情况

  摘要：

  在有机合成或聚合物化学中寻找对烯烃加成反应具有低选择性和高反应性的新的自由基结构可能是有机合成或聚合物化学中的重要问题，这促使我们提出了一种新的四唑衍生的噻吩基。将这种以硫为中心的结构的反应性与同样对烯烃加成有效的氨基烷基的反应性进行了比较。对于缺电子（丙烯腈，...）或富电子（乙烯基醚，...）的双分子，新结构在整个烯烃范围内均具有更高的反应性，且加成速率常数高于10 7 M -1 s -1债券。量子力学计算可以更好地理解这一独特功能。

  DOI：

  10.1021/jo061793w