1-methyl-4-(4-nitrophenyl)-1H-tetrazole-5(4H)-thione | 1187680-35-8

• 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-methyl-4-(4-nitrophenyl)-1H-tetrazole-5(4H)-thione
• CAS: 1187680-35-8
• 化学式: C₈H₇N₅O₂S
• 分子量: 237.242
• InChiKey: FIQVVYACQAKREN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.78
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  4-methyl-1-(4-nitrophenyl)tetrazol-5-one 在 tetraphosphorus decasulfide 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以50%的产率得到1-methyl-4-(4-nitrophenyl)-1H-tetrazole-5(4H)-thione
  参考文献：
  名称：

  Electronic properties of 1-methyl-4-phenyl-1H-tetrazole-5(4H)-thiones: An experimental and theoretical study

  摘要：

  The syntheses of 1-(4-methoxyphenyl)1-4-methyl-1H-tetrazol-5(4H)-thione 1a, 1-methyl-4-phenyl-1H-tetrazole-5(4H)-thione 1b, 1-(4-chlorophenyt)-4-methyl-1H-tetrazol-5(4H)-thione 1c, 1-methyl-4-(4-nitrophenyl)-1H-tetrazol-5(4H)-thione 1d were carried out and their electronic absorption spectra were obtained in cyclohexane, THF, and acetonitrile. The UV spectra of la-d showed a modest dependence on the polarity of the solvent. The change of substituent on the tetrazolethione ring from a strongly electron donating group (p-C6H4OMe, 1a), to a moderately electron donating (C6H5, 1b) to a weakly electron withdrawing group (p-C6H4Cl, 1c) also produced minimal effect on the electronic properties of la-c. However, the presence of a strongly electron withdrawing group (p-C6H4NO2, 1d) on the heterocyclic ring produced a marked change in the UV spectrum. Time-dependent density functional calculations revealed that all the bands result from pi ->pi* excitations with some degree of intramolecular charge transfer (ICT) within the molecules. Our studies further showed that as the acceptor strength is increased in the order: la (p-C6H4OMe) < 1b (C6H5) < 1c (p-C6H4Cl) < 1d (p-C6H4NO2), the ICT also increases. In accordance with the experimental observations, the calculated transitions also showed modest dependence on the polarity of the solvent. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2009.05.049