bis(1-naphthylthionyl) disulfide | 39969-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: bis(1-naphthylthionyl) disulfide
• 英文别名: bis(1-thionaphthoyl)-disulfide；bis-[1]thionaphthoyl-disulfane；Bis-[1]thionaphthoyl-disulfan；Bis-(thio-α-naphthoyl)-disulfid；Bis-(α-thionaphthyl)-disulfid；Naphthalene-1-carbothioylsulfanyl naphthalene-1-carbodithioate
• CAS: 39969-88-5
• 化学式: C₂₂H₁₄S₄
• 分子量: 406.617
• InChiKey: XHBHOMZWLVPWQO-UHFFFAOYSA-N

物化性质

• 熔点：
  169-170 °C
• 沸点：
  606.8±38.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(1-naphthylthionyl) disulfide 在 sodium hydroxide 、 盐酸羟胺 、 sodium carbonate 作用下， 以 氯仿 为溶剂， 生成 1-Naphthothiohydroxamsaeure
  参考文献：
  名称：

  Mitchell,A.J. et al., Australian Journal of Chemistry, 1977, vol. 30, p. 2439 - 2453

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴甲基萘 在 sodium methylate 、 sulfur 、 碘 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 bis(1-naphthylthionyl) disulfide
  参考文献：
  名称：

  Searching for More Effective Agents and Conditions for the RAFT Polymerization of MMA:  Influence of Dithioester Substituents, Solvent, and Temperature

  摘要：

  A series of tertiary dithiobenzoates differently substituted on the phenyl group (Z) were synthesized in order to investigate the RAFT-mediated polymerization of MMA. The chain-transfer agent 2-eyanoprop-2-yl dithiobenzoate, although an excellent RAFT agent for polymerization of MMA, does not yield a very narrow polydispersed polymer at low conversion. The introduction of electron-withdrawing substituents on the dithiobenzoate aromatic ring improves the activity of the chain-transfer agent narrowing the molecular weight distribution, especially in the first 2 h of the process; conversely, electron-donating substituents deteriorate the performance of the process in the early stages. Substituents on the dithiobenzoate that, for reasons of steric hindrance reduce the conjugation of the phenyl with the C=S double bond of the dithiogroup, diminish the effectiveness of the chain-transfer agent. The nature of the leaving group (R) also has a strong influence on the process: the substitution of 2-cyanoprop-2-yl with the bulkier 2-cyano-4-methylpent-2-yl as leaving group improves remarkably the MMA polymerization, especially in the early stages. The solvent effect on MMA RAFT polymerization using benzene, acetonitrile, and DMF was also investigated. The lower propagation rate constant of MMA in benzene gives rise to reduced rates of polymerization but narrower polydispersities of the polymer, especially at low conversions. The RAFT polymerizations of MMA were carried out at 60 and 90 degrees C to assess the temperature dependence of the process. The higher temperature increases both the rate of polymerization and the transfer constant of the RAFT agent, resulting in lower polydispersities at a given conversion. Ab initio calculations confirmed the observed experimental results.

  DOI：

  10.1021/ma0480650

文献信息

• Schoenberg et al., Chemische Berichte, 1933, vol. 66, p. 245,249
  作者：Schoenberg et al.

  DOI：——

  日期：——
• Houben, Chemische Berichte, 1906, vol. 39, p. 3229
  作者：Houben

  DOI：——

  日期：——
• Schoenberg, Chemische Berichte, 1935, vol. 68, p. 163
  作者：Schoenberg

  DOI：——

  日期：——
• Schoenberg; Barakat, Journal of the Chemical Society, 1949, p. 892
  作者：Schoenberg、Barakat

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Ag: MVol.B7, 1.20.4, page 94 - 96
  作者：

  DOI：——

  日期：——