2-cyano-2-propyl p-nitrobenzenesulfonate | 99072-50-1

• 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-cyano-2-propyl p-nitrobenzenesulfonate
• 英文别名: 4-Nitro-benzolsulfonsaeure-<α-cyan-isopropylester>；4-Nitro-benzolsulfonsaeure-(α-cyan-isopropylester)
• CAS: 99072-50-1
• 化学式: C₁₀H₁₀N₂O₅S
• 分子量: 270.266
• InChiKey: DTLZMCIBMBSMDP-UHFFFAOYSA-N

物化性质

• 熔点：
  63.5-64.5 °C
• 沸点：
  460.6±25.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  110.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-cyano-2-propyl p-nitrobenzenesulfonate 、 乙烷,三氯氟- 以 乙腈 为溶剂， 生成 4-nitro-N-(p-tolyl)benzenesulfonamide
  参考文献：
  名称：

  Bimolecular nucleophilic displacement at tertiary carbon centers: Aminolyses of 2-cyano-2-propyl and 1-cyanocyclooctyl arenesulfonates

  摘要：

  Kinetic studies were carried out on the reactions of anilines with 2-cyano-2-propyl and 1-cyanocyclooctyl arenesulfonates in acetonitrile at 50.0 degrees C. The second-order rate constants for the former are in general greater than those for the latter but the rates of the two become comparable for a strong nucleofuge, The cross-interaction constants, rho(XZ) (and beta(XZ)), are considerably smaller (ca -0.04) than those for the primary (ca 0.33) and secondary (ca 0.12) compounds, The negative sign and small magnitude are consistent with a dissociative S(N)2 mechanism with a loose transition state structure. The ab initio MO theoretical results for Cl- + RCl reversible arrow ClR + Cl- at the MP2 level (MP2/6-31 + G*//MP2/6-31 + G*) confirm the,looseness of the transition state for the tertiary (R) alkyl compounds. The average r((Cl ... Cl))* value is 4.88 +/- 0.03 Angstrom, which is larger than those for the reactions at primary (4.68 +/- 0.02 Angstrom) and secondary (4.80 +/- 0.02 Angstrom) carbon centers. Thus a looser transition state with a smaller magnitude of rho(XZ) for the tertiary carbon centers has a larger theoretical r((Cl ... Cl))* value.

  DOI：

  10.1002/(sici)1099-1395(199610)9:10<683::aid-poc840>3.0.co;2-k
• 作为产物：
  描述：

  氰化钾 、 p-nitrobenzenesulfonic anhydride 、 丙酮 在 吡啶 、 sodium hydrogensulfite 作用下， 生成 2-cyano-2-propyl p-nitrobenzenesulfonate
  参考文献：
  名称：

  Bimolecular nucleophilic displacement at tertiary carbon centers: Aminolyses of 2-cyano-2-propyl and 1-cyanocyclooctyl arenesulfonates

  摘要：

  Kinetic studies were carried out on the reactions of anilines with 2-cyano-2-propyl and 1-cyanocyclooctyl arenesulfonates in acetonitrile at 50.0 degrees C. The second-order rate constants for the former are in general greater than those for the latter but the rates of the two become comparable for a strong nucleofuge, The cross-interaction constants, rho(XZ) (and beta(XZ)), are considerably smaller (ca -0.04) than those for the primary (ca 0.33) and secondary (ca 0.12) compounds, The negative sign and small magnitude are consistent with a dissociative S(N)2 mechanism with a loose transition state structure. The ab initio MO theoretical results for Cl- + RCl reversible arrow ClR + Cl- at the MP2 level (MP2/6-31 + G*//MP2/6-31 + G*) confirm the,looseness of the transition state for the tertiary (R) alkyl compounds. The average r((Cl ... Cl))* value is 4.88 +/- 0.03 Angstrom, which is larger than those for the reactions at primary (4.68 +/- 0.02 Angstrom) and secondary (4.80 +/- 0.02 Angstrom) carbon centers. Thus a looser transition state with a smaller magnitude of rho(XZ) for the tertiary carbon centers has a larger theoretical r((Cl ... Cl))* value.

  DOI：

  10.1002/(sici)1099-1395(199610)9:10<683::aid-poc840>3.0.co;2-k