4-nitrophenyl dithioacetate | 144735-08-0

• 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: 4-nitrophenyl dithioacetate
• 英文别名: (4-Nitrophenyl) ethanedithioate
• CAS: 144735-08-0
• 化学式: C₈H₇NO₂S₂
• 分子量: 213.281
• InChiKey: KTXAGNADYDKSSA-UHFFFAOYSA-N

物化性质

• 沸点：
  354.3±44.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-羟乙基哌嗪 、 4-nitrophenyl dithioacetate 以 水 为溶剂， 生成 1-[4-(2-Hydroxy-ethyl)-piperazin-1-yl]-ethanethione 、 4-硝基苯硫醇
  参考文献：
  名称：

  Kinetics and mechanism of the aminolysis of 4-nitrophenyl dithioacetate

  摘要：

  The reaction of the title substrate with a series of secondary alicylic amines has been the subject of a kinetic study in aqueous solution, 25-degrees-C, ionic strength 0.2 M (KCl). With the amine in excess, pseudo-first-order rate constants (k(obsd)) are observed. The order in amine varies from 1 to 2 depending on the basicity of the amine and the reaction conditions. A reaction scheme is deduced on the basis of the existence of zwitterionic (T+/-) and anionic (T-) tetrahedral intermediates. Proton transfer from T+/- to an amine or base (to yield T-) seems to compete with 4-nitrothiophenoxide (NPS-) expulsion from T+/-. The pK(a) of T+/- and all the rate microconstants of the scheme are estimated. The rates of expulsion of NPS- and amine from T+/- are smaller than those from analogous T+/- formed in the aminolyses of O-ethyl S-(4-nitrophenyl) dithiocarbonate and 4-nitrophenyl thiolacetate. It is claimed that substitution of Me by RO (R = alkyl) or S- by O- in T+/- destablizes this intermediate.

  DOI：

  10.1021/jo00052a010
• 作为产物：
  描述：

  4-硝基苯基硫酚乙酸酯 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 4-nitrophenyl dithioacetate
  参考文献：
  名称：

  Kinetics and mechanism of the aminolysis of 4-nitrophenyl dithioacetate

  摘要：

  The reaction of the title substrate with a series of secondary alicylic amines has been the subject of a kinetic study in aqueous solution, 25-degrees-C, ionic strength 0.2 M (KCl). With the amine in excess, pseudo-first-order rate constants (k(obsd)) are observed. The order in amine varies from 1 to 2 depending on the basicity of the amine and the reaction conditions. A reaction scheme is deduced on the basis of the existence of zwitterionic (T+/-) and anionic (T-) tetrahedral intermediates. Proton transfer from T+/- to an amine or base (to yield T-) seems to compete with 4-nitrothiophenoxide (NPS-) expulsion from T+/-. The pK(a) of T+/- and all the rate microconstants of the scheme are estimated. The rates of expulsion of NPS- and amine from T+/- are smaller than those from analogous T+/- formed in the aminolyses of O-ethyl S-(4-nitrophenyl) dithiocarbonate and 4-nitrophenyl thiolacetate. It is claimed that substitution of Me by RO (R = alkyl) or S- by O- in T+/- destablizes this intermediate.

  DOI：

  10.1021/jo00052a010

文献信息

• Kinetics and mechanism of the aminolysis of 4-nitrophenyl dithioacetate
  作者：Enrique A. Castro、Fernando Ibanez、Jose G. Santos、Carmen Ureta

  DOI：10.1021/jo00052a010

  日期：1992.12

  The reaction of the title substrate with a series of secondary alicylic amines has been the subject of a kinetic study in aqueous solution, 25-degrees-C, ionic strength 0.2 M (KCl). With the amine in excess, pseudo-first-order rate constants (k(obsd)) are observed. The order in amine varies from 1 to 2 depending on the basicity of the amine and the reaction conditions. A reaction scheme is deduced on the basis of the existence of zwitterionic (T+/-) and anionic (T-) tetrahedral intermediates. Proton transfer from T+/- to an amine or base (to yield T-) seems to compete with 4-nitrothiophenoxide (NPS-) expulsion from T+/-. The pK(a) of T+/- and all the rate microconstants of the scheme are estimated. The rates of expulsion of NPS- and amine from T+/- are smaller than those from analogous T+/- formed in the aminolyses of O-ethyl S-(4-nitrophenyl) dithiocarbonate and 4-nitrophenyl thiolacetate. It is claimed that substitution of Me by RO (R = alkyl) or S- by O- in T+/- destablizes this intermediate.