3-cyanoquinuclidine hydrochloride | 116599-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: 3-cyanoquinuclidine hydrochloride
• 英文别名: quinuclidine-3-carbonitrile; hydrochloride；Chinuclidin-3-carbonitril; Hydrochlorid
• CAS: 116599-22-5
• 化学式: C₈H₁₂N₂*ClH
• 分子量: 172.658
• InChiKey: KMGSVWGQRJDDAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.03
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  对甲基苯磺酰甲基异腈 、 3-奎宁环酮盐酸盐 在 potassium tert-butylate 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 1.0h， 以0.9 g的产率得到3-cyanoquinuclidine hydrochloride
  参考文献：
  名称：

  Does dissociation of amine water complexes depend upon amine basicity? Proton exchange between quinuclidinium ions and solvent

  摘要：

  The rate of proton exchange between 3-X-quinuclidinium ions (X = H, OH, Cl, and CN) and solvent water was studied by dynamic H-1 NMR techniques. The rate constants show a pH dependence expected for the Swain-Grunwald mechanism, with a pH-independent region above pH almost-equal-to 1 and the characteristic inhibition at lower pH values. The rate constants for breaking the R3N.HOH hydrogen bond, k(H), range from 1.9 x 10(9) s-1 for X = H to 1.2 x 10(10) s-1 for X = CN, and show a dependence on the base strength of R3N with a Bronsted plot slope of beta-diss = -0.25 +/- 0.04. A molecular mechanics computation on complexes of representative model compounds and solvent molecules of different sizes indicates that the London dispersion contribution to the interaction enthalpy only accounts for a minor fraction of the dissociation barrier, at variance with earlier findings of Grunwald and co-workers. It is suggested that the rate of dissociation of amine-water or amine-alcohol complexes is primarily determined by the Gibbs free energy contributions from the pK(a)-dependent hydrogen-bond breaking, dispersion forces between acceptor and donor, and the energy required to create a cavity prior to dissociation.

  DOI：

  10.1021/ja00018a043