| 184168-94-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• CAS: 184168-94-3
• 化学式: C₂H₅S₂
• 分子量: 93.1937
• InChiKey: IXBUFAUQDFHNGI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  4.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  二甲基二硫 在 α-methylbenzyl anion 作用下， 26.9 ℃ 、40.0 Pa 条件下， 生成 methanethiolate 、
  参考文献：
  名称：

  Dimethyl disulfide: anion-molecule reactions in the gas phase at 300 K

  摘要：

  DOI：

  10.1021/ja00186a005

文献信息

• Anion Structure Determination in the Gas Phase:  Chemical Reactivity as a Probe
  作者：Jeehiun K. Lee、Joseph J. Grabowski

  DOI：10.1021/jo961463j

  日期：1996.1.1

  In the gas phase, the discrimination between two isomeric anion structures is a challenge that requires different solutions for different applications. The anionic oxy-Cope rearrangement involves the rearrangement of an alkoxide to an isomeric enolate; the mechanistic study of such a process in the gas phase requires a simple and selective probe process. Using a flowing afterglow mass spectrometer, we have examined the utility and limitations of using chemical reactivity to discriminate between alkoxides and enolates in the gas phase. A series of alkoxides and enolates were allowed to react with three chemical probe reagents: methanol-O-d, methyl nitrite, and dimethyl disulfide. Quantitative and qualitative characterization of each probe reagent reveals the especially broad and flexible utility of dimethyl disulfide as a chemical probe. Dimethyl disulfide is a selective reagent with ambident behavior that reacts efficiently with all anions studied and fully capitalizes on the structure/reactivity differences between alkoxides and enolates. Alkoxides behave as classical ''hard bases'' when allowed to react with dimethyl disulfide, effecting elimination across the C-S bond, whereas enolates, ''soft bases'', attack at sulfur. Methyl nitrite is also a selective ambident probe reagent but, due to its particularly slow reaction with enolates, is useful only in conjunction with a more reliable probe such as dimethyl disulfide. Methanol-O-d, for a variety of reasons detailed in the paper, is unsuitable as a chemical probe reagent for the unequivocal discernment between alkoxides and enolates.