| 180908-02-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 180908-02-5
• 化学式: C₂₈H₄₀N₂Se₂
• 分子量: 564.546
• InChiKey: SGMBZSDMDRMBSC-WGBSZODISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  6.48
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  在 磺酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 15N-2-[(N-cyclohexyl-N-methylamino)methyl]benzeneselenyl chloride
  参考文献：
  名称：

  Nature of the Intramolecular Se···N Nonbonded Interaction of 2-Selenobenzylamine Derivatives. An Experimental Evaluation by ¹H, ⁷⁷Se, and ¹⁵N NMR Spectroscopy

  摘要：

  H-1 NMR analysis of seven 2-selenobenzylamine derivatives (ArSeX, 1-7) has revealed the existence of attractive nonbonded interaction between the divalent selenium and an unsymmetric amino nitrogen, whose strength significantly depends on the relative electrophilic reactivity of the selenium moiety. In the intermediate cases (5, X=CN; 6, X=SPh), the dissociation energy of the Se ... N nonbonded interaction was evaluated as 12.4 and 10.8 kcal/mol, respectively, by variable-temperature H-1 NMR spectral simulations. The corresponding values were roughly estimated as >18.8 kcal/mol for the strong cases (2, X=Br; 3, X=Cl; 4, X=OAc) and <7.7 kcal/mol for the weak cases (1, X=SeAT; 7, X=Me). In order to elucidate physicochemical properties of the interactilon, N-15-labeled compounds were synthesized. Downfield shifts of N-15 NMR (Delta delta(N)) and increment of J(Se ... N) (coupling constant between Se-77 and N-15) were observed with increasing Se ... N interaction. In the case of strong Se ... N interaction, saturation of coupling constants was observed. These experimental observations as well as large NBO deletion energies (3-21G* and LANL1DZ) between the selenium and the nitrogen for model compounds (9-13) strongly suggested that the observed Se ... N interaction is mainly caused by the orbital interaction between the nitrogen lone pair (n(N)) and the antibonding orbital of the Se-X bond (sigma*(Se-X)).

  DOI：

  10.1021/ja953358h
• 作为产物：
  描述：

  cyclohexylmethylamine-15N 、 bis<(2-chloromethyl)phenyl> diselenide 在 碳酸氢钠 、 potassium iodide 作用下， 生成
  参考文献：
  名称：

  Nature of the Intramolecular Se···N Nonbonded Interaction of 2-Selenobenzylamine Derivatives. An Experimental Evaluation by ¹H, ⁷⁷Se, and ¹⁵N NMR Spectroscopy

  摘要：

  H-1 NMR analysis of seven 2-selenobenzylamine derivatives (ArSeX, 1-7) has revealed the existence of attractive nonbonded interaction between the divalent selenium and an unsymmetric amino nitrogen, whose strength significantly depends on the relative electrophilic reactivity of the selenium moiety. In the intermediate cases (5, X=CN; 6, X=SPh), the dissociation energy of the Se ... N nonbonded interaction was evaluated as 12.4 and 10.8 kcal/mol, respectively, by variable-temperature H-1 NMR spectral simulations. The corresponding values were roughly estimated as >18.8 kcal/mol for the strong cases (2, X=Br; 3, X=Cl; 4, X=OAc) and <7.7 kcal/mol for the weak cases (1, X=SeAT; 7, X=Me). In order to elucidate physicochemical properties of the interactilon, N-15-labeled compounds were synthesized. Downfield shifts of N-15 NMR (Delta delta(N)) and increment of J(Se ... N) (coupling constant between Se-77 and N-15) were observed with increasing Se ... N interaction. In the case of strong Se ... N interaction, saturation of coupling constants was observed. These experimental observations as well as large NBO deletion energies (3-21G* and LANL1DZ) between the selenium and the nitrogen for model compounds (9-13) strongly suggested that the observed Se ... N interaction is mainly caused by the orbital interaction between the nitrogen lone pair (n(N)) and the antibonding orbital of the Se-X bond (sigma*(Se-X)).

  DOI：

  10.1021/ja953358h