N,N-dimethyl-o-nitrobenzenesulfenamide | 24398-41-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-dimethyl-o-nitrobenzenesulfenamide
• 英文别名: Benzenesulfenamide, N,N-dimethyl-2-nitro-；N-methyl-N-(2-nitrophenyl)sulfanylmethanamine
• CAS: 24398-41-2
• 化学式: C₈H₁₀N₂O₂S
• 分子量: 198.246
• InChiKey: JRSDDRLHIUFQFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-o-nitrobenzenesulfenamide 在 三氟甲磺酸 甲醇 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Mechanism of nucleophilic substitution reactions of o-nitrobenzenesulfenamides: evidence for a substitution proceeding through a sulfuranide intermediate

  摘要：

  o-Nitrobenzenesulfenamides (1) undergo acid-catalyzed methanolysis (eq 2) in acetonitrile-methanol, affording methyl o-nitrobenzenesulfenate (2). They also undergo acid-catalyzed reaction with a thiol, giving an alkyl o-nitrophenyl disulfide (eq 3). In MeCN-8.2 M MeOH the thiolysis reaction exhibits a simple first-order dependence on both [R'SH] and [H+] for acid concentrations in the range 0.001-0.012 M. In marked contrast the rate of the methanolysis reaction is only slightly dependent on [H+] for the same range of acid concentrations. It is also markedly dependent on [MeOH], being seven times faster in MeCN-8.2 M MeOH than in MeCN-3.0 M MeOH. Measurement of the equilibrium constant for protonation of 1 to 1-H+ in MeCN-8.2 M MeOH shows that under the conditions used for the kinetic studies of eqs 2 and 3 the extent of protonation of 1 to 1-H+ is always small (<6%). Consideration of this fact, and the markedly different kinetic behavior of the two substitution reactions, leads to the following interpretation: (a) for the thiolysis the rate-determining step is the reaction of the thiol with 1-H+; (b) for the methanolysis, on the other hand, the mechanism is that shown in eq 9, where a sulfuranide species 4 is the key intermediate on the reaction coordinate. The lack of dependence of the rate on [H+] is because acid-catalyzed reversion of 4 to 1-H+ and methanol (Step k-6) is faster than the cleavage of 4 (step k7) to give 2 and R2NH. The methanolysis of 1 therefore represents another substitution at dicoordinate sulfur (similar to ref 10) where the kinetics require a mechanism with a hypervalent sulfur species as an intermediate on the reaction coordinate.

  DOI：

  10.1021/jo00038a013
• 作为产物：
  描述：

  2-nitrobenzenesulfenyl bromide 在 甲醇 、 二硫化碳 作用下， 生成 N,N-dimethyl-o-nitrobenzenesulfenamide
  参考文献：
  名称：

  Foss, Acta Chemica Scandinavica (1947), 1947, vol. 1, p. 307,316

  摘要：

  DOI：

文献信息

• Levchenko,E.S.; Seleznenko,L.V., Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, p. 144 - 148
  作者：Levchenko,E.S.、Seleznenko,L.V.

  DOI：——

  日期：——
• Zincke; Farr, Justus Liebigs Annalen der Chemie, 1912, vol. 391, p. 87
  作者：Zincke、Farr

  DOI：——

  日期：——
• Zincke, Chemische Berichte, 1911, vol. 44, p. 770
  作者：Zincke

  DOI：——

  日期：——
• SOME NEW METHODS FOR PREPARING BUNTE SALTS
  作者：HANS Z. LECHER、ELIZABETH M. HARDY

  DOI：10.1021/jo01122a010

  日期：1955.4
• Ruostesuo, Pirkko; Haekkinen, Anna-Maija; Kivekaes, Raikko, Journal of the Chemical Society. Perkin transactions II, 1989, p. 1397 - 1404
  作者：Ruostesuo, Pirkko、Haekkinen, Anna-Maija、Kivekaes, Raikko、Sundberg, Markku R.

  DOI：——

  日期：——