2-nitroethylbenzene | 128575-87-1

• 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: 2-nitroethylbenzene
• CAS: 128575-87-1
• 化学式: C₈H₈NO₂
• 分子量: 150.157
• InChiKey: SZJBTJJIJPNWMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 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：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-nitroethylbenzene 在 pyridin-1-ium 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以100%的产率得到Β-硝基苯乙烷
  参考文献：
  名称：

  Luening, Ulrich; Schillinger, Fritz, Chemische Berichte, 1990, vol. 123, # 10, p. 2073 - 2075

  摘要：

  DOI：
• 作为产物：
  描述：

  Β-硝基苯乙烷 在 18-冠醚-6 、 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 生成 2-nitroethylbenzene
  参考文献：
  名称：

  Luening, Ulrich; Schillinger, Fritz, Chemische Berichte, 1990, vol. 123, # 10, p. 2073 - 2075

  摘要：

  DOI：

文献信息

• Carbanion Stabilization by Adjacent Sulfur:  Polarizability, Resonance, or Negative Hyperconjugation? Experimental Distinction Based on Intrinsic Rate Constants of Proton Transfer from (Phenylthio)nitromethane and 1-Nitro-2-phenylethane
  作者：Claude F. Bernasconi、Kevin W. Kittredge

  DOI：10.1021/jo9719463

  日期：1998.3.1

  (Phenylthio)nitromethane, PhSCH2NO2, is about as acidic as PhCH2NO2 and about 4 pK(a)-units more acidic than CH3NO2 in water or aqueous DMSO, showing the well-known acidifying effect of thio substituents in the alpha-position of carbon acids. Over the years various interpretations have been offered for the acidifying effect of sulfur groups: d-p pi-resonance, polarizability, and negative hyperconjugation. Assuming that the nature of the factors that potentially stabilize the transition state of the proton transfer from the carbon acid are the same as those that potentially stabilize the carbanion, we show that a distinction between these interpretations can be based on the effect of the phenylthio group on the intrinsic rate constants (k(0)) of proton transfer. Such intrinsic rate constants were determined for the deprotonation of PhSCH2NO2 and PhCH2CH2NO2 by amines in water and 90% DMSO-10% water; in both solvents k(0) for PhSCH2NO2 was found to be substantially higher than for PhCH2CH2NO2 as well as for other nitroalkanes reported previously. Based on a detailed analysis of how various factors such as resonance, inductive effects, polarizability, and positive and negative hyperconjugation affect the intrinsic rate constants for proton transfer, it is concluded that the high k(0) values for PhSCH2NO2 result from a combination of the inductive and polarizability effect of the PhS group and that d-p pi-resonance and negative hyperconjugation play a minor role if any.
• Luening, Ulrich; Schillinger, Fritz, Chemische Berichte, 1990, vol. 123, # 10, p. 2073 - 2075
  作者：Luening, Ulrich、Schillinger, Fritz

  DOI：——

  日期：——