N-<(4-methylphenyl)thio>-2,4,6-triphenylaniline | 136489-93-5

• 英文名称: N-<(4-methylphenyl)thio>-2,4,6-triphenylaniline
• 英文别名: N-(4-methylphenyl)sulfanyl-2,4,6-triphenylaniline
• CAS: 136489-93-5
• 化学式: C₃₁H₂₅NS
• 分子量: 443.612
• InChiKey: KBKJZLAEELQVFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲基苯硫氯 、 2,4,6-三苯基苯胺 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以11%的产率得到N-<(4-methylphenyl)thio>-2,4,6-triphenylaniline
  参考文献：
  名称：

  ESR studies of nitrogen-centered free radicals. 40. Exceptionally persistent nitrogen-centered free radicals. Preparation, isolation, and molecular structure of N-(arylthio)-2,4,6-triphenylanilino radicals

  摘要：

  The preparation, isolation, molecular structure, and ESR spectra of N-(arylthio)-2,4,6-triphenylanilino radicals 2 are described. Radicals 2 have been prepared by oxidation of N-(arylthio)-2,4,6-triphenylaniline (1) with PbO2 and studied by ESR spectroscopy. The radical solutions (benzene) were greenish blue or yellowish green, absorbing in the visible region at 513-535 and 626-644 nm. The radicals persist over a long period with only a slight or no decomposition, even in the presence of atmospheric oxygen, and have shown no tendency to dimerize, even at low temperatures. These properties have permitted us to isolate 2 as pure radical crystals and to determine the molecular structure of 2e by single-crystal X-ray analysis. The ESR spectrum of 2 consists of a broad 1:1:1 triplet (alpha-N, 0.890-0.896 mT), and hyperfine splittings due to protons were completely unresolved. However, on deuteriation of the 2,4,6-triphenyl groups on the anilino group, hyperfine splittings due to the anilino meta (0.133-0.134) and the arylthiyl ortho protons (0.088 mT) were found. Furthermore, at high gain satellite lines due to S-33 isotopes (0.51 mT) at natural abundance were detected. On the basis of these ESR results the spin density distribution in 2 is elucidated.

  DOI：

  10.1021/jo00023a032