4-chloro-N-[2-nitro-2-(4-nitrophenyl)-1-phenylethyl]aniline

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-chloro-N-[2-nitro-2-(4-nitrophenyl)-1-phenylethyl]aniline
• 化学式: C₂₀H₁₆ClN₃O₄
• 分子量: 397.818
• InChiKey: NLPSUZWBLPXVGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-硝基-4-(硝基甲基)苯 、 N-亚苄基-4-氯苯胺 在 二乙胺 作用下， 以 乙醇 为溶剂， 反应 0.02h， 以84%的产率得到4-chloro-N-[2-nitro-2-(4-nitrophenyl)-1-phenylethyl]aniline
  参考文献：
  名称：

  Large Transition State Imbalance in the Expulsion of Arylnitromethane Anions from Aniline Adducts of .alpha.-Nitrostilbenes

  摘要：

  Aniline adducts of alpha-nitrostilbenes, PhCH(HNC(6)H(4)Z)CH(C6H4Y)NO2 have been synthesized for a variety of Z/Y combinations. In several cases a mixture of two diastereomers was obtained. Structural assignment of the diastereomers was based both on H-1 NMR and reactivity data. The kinetics of the breakdown of the adducts into the respective benzalanilines and arylnitromethane anions was studied in acidic 50% Me(2)SO-50% water solutions at 5 degrees C. The rate constants, h(exp), were found to be independent of buffer concentration and pH, indicating a unimolecular mechanism. There is a strong dependence on the aniline substituent (rho = -2.2) and the pK(a) of the arylnitromethanes (beta(1g) = -1.28). By estimating the substituent dependence of the equilibrium constant (K-exp), approximate normalized structure-reactivity parameters alpha(exp)(n)=(dlog K-exp)(Z) approximate to 1.28 and beta(exp)(n)=(dlog k(exp)/dlog K-exp)Y approximate to 0.58 have been calculated. This suggests the presence of a substantial transition state imbalance (alpha(exp)(n)-beta(exp)(n) approximate to 0.70), similar to that in the deprotonation of arylnitromethanes.

  DOI：

  10.1021/jo00097a051

文献信息

• Large Transition State Imbalance in the Expulsion of Arylnitromethane Anions from Aniline Adducts of .alpha.-Nitrostilbenes
  作者：Claude F. Bernasconi、Richard A. Renfrow

  DOI：10.1021/jo00097a051

  日期：1994.9

  Aniline adducts of alpha-nitrostilbenes, PhCH(HNC(6)H(4)Z)CH(C6H4Y)NO2 have been synthesized for a variety of Z/Y combinations. In several cases a mixture of two diastereomers was obtained. Structural assignment of the diastereomers was based both on H-1 NMR and reactivity data. The kinetics of the breakdown of the adducts into the respective benzalanilines and arylnitromethane anions was studied in acidic 50% Me(2)SO-50% water solutions at 5 degrees C. The rate constants, h(exp), were found to be independent of buffer concentration and pH, indicating a unimolecular mechanism. There is a strong dependence on the aniline substituent (rho = -2.2) and the pK(a) of the arylnitromethanes (beta(1g) = -1.28). By estimating the substituent dependence of the equilibrium constant (K-exp), approximate normalized structure-reactivity parameters alpha(exp)(n)=(dlog K-exp)(Z) approximate to 1.28 and beta(exp)(n)=(dlog k(exp)/dlog K-exp)Y approximate to 0.58 have been calculated. This suggests the presence of a substantial transition state imbalance (alpha(exp)(n)-beta(exp)(n) approximate to 0.70), similar to that in the deprotonation of arylnitromethanes.