1-(¹⁵N)octadecylamine | 85541-40-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(¹⁵N)octadecylamine
• 英文别名: n-(¹⁵N)octadecylamine；octadecan-1-(15N)amine
• CAS: 85541-40-8
• 化学式: C₁₈H₃₉N
• 分子量: 270.508
• InChiKey: REYJJPSVUYRZGE-QHPTYGIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  19
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(¹⁵N)octadecylamine 、 1-(¹⁵N)napthylisothiocyanate 以 氯仿 为溶剂， 反应 0.25h， 以90%的产率得到¹⁵N-(1-naphthyl),¹⁵N-(n-octadecyl)thiourea
  参考文献：
  名称：

  Evidence of Entropy-Driven Bistability through ¹⁵N NMR Analysis of a Temperature- and Solvent-Induced, Chiroptical Switching Polycarbodiimide

  摘要：

  The thermo- and solvo-driven chiroptical switching process observed in specific polycarbodiimides occurs in a concerted fashion with large deviations in specific optical rotation (OR) and CD Cotton effect as a consequence of varying populations of two distinct polymer conformations. These two conformations are clearly visible in the N-15 NMR and IR spectra of the N-15-labeled poly(N-15-(1-naphthyl)-N'-octadecylcarbodiimide) (Poly-3) and poly(N-15-(1-naphthyl)-N-15'-octadecylcarbodiimide) (Poly-5). Using van't Hoff analysis, the enthalpies and entropies of switching (Delta H-switching; Delta S-switching) were calculated for both Poly-3 and Poly-5 using the relative integrations of both peaks in the N-15 NMR spectra at different temperatures to measure the populations of each state. The chiroptical switching (i.e., transitioning from state A to state B) was found to be an endothermic process (positive Delta H-switching) for both Poly-3 and Poly-5 in all solvents studied, meaning the conformation correlating with the downfield chemical shift (ca. 148 ppm, state B) is the higher enthalpy state. The compensating factor behind this phenomenon has been determined to be the large increase in entropy in CHCl3 as a result of the switching. Herein, we propose that the increased entropy in the system is a direct consequence of increased disorder in the solvent as the switching occurs. Specifically, the chloroform solvent molecules are very ordered around the polymer chains due to favorable solvent-polymer interactions, but as the switching occurs, these interactions become less favorable and disorder results. The same level of solvent disorder is not achieved in toluene, causing the chiroptical switching process to occur at higher temperatures.

  DOI：

  10.1021/ja4098803
• 作为产物：
  描述：

  硬脂基溴 在 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 1-(¹⁵N)octadecylamine
  参考文献：
  名称：

  Evidence of Entropy-Driven Bistability through ¹⁵N NMR Analysis of a Temperature- and Solvent-Induced, Chiroptical Switching Polycarbodiimide

  摘要：

  The thermo- and solvo-driven chiroptical switching process observed in specific polycarbodiimides occurs in a concerted fashion with large deviations in specific optical rotation (OR) and CD Cotton effect as a consequence of varying populations of two distinct polymer conformations. These two conformations are clearly visible in the N-15 NMR and IR spectra of the N-15-labeled poly(N-15-(1-naphthyl)-N'-octadecylcarbodiimide) (Poly-3) and poly(N-15-(1-naphthyl)-N-15'-octadecylcarbodiimide) (Poly-5). Using van't Hoff analysis, the enthalpies and entropies of switching (Delta H-switching; Delta S-switching) were calculated for both Poly-3 and Poly-5 using the relative integrations of both peaks in the N-15 NMR spectra at different temperatures to measure the populations of each state. The chiroptical switching (i.e., transitioning from state A to state B) was found to be an endothermic process (positive Delta H-switching) for both Poly-3 and Poly-5 in all solvents studied, meaning the conformation correlating with the downfield chemical shift (ca. 148 ppm, state B) is the higher enthalpy state. The compensating factor behind this phenomenon has been determined to be the large increase in entropy in CHCl3 as a result of the switching. Herein, we propose that the increased entropy in the system is a direct consequence of increased disorder in the solvent as the switching occurs. Specifically, the chloroform solvent molecules are very ordered around the polymer chains due to favorable solvent-polymer interactions, but as the switching occurs, these interactions become less favorable and disorder results. The same level of solvent disorder is not achieved in toluene, causing the chiroptical switching process to occur at higher temperatures.

  DOI：

  10.1021/ja4098803

文献信息

• Evidence of Entropy-Driven Bistability through ¹⁵N NMR Analysis of a Temperature- and Solvent-Induced, Chiroptical Switching Polycarbodiimide
  作者：James F. Reuther、Bruce M. Novak

  DOI：10.1021/ja4098803

  日期：2013.12.26

  The thermo- and solvo-driven chiroptical switching process observed in specific polycarbodiimides occurs in a concerted fashion with large deviations in specific optical rotation (OR) and CD Cotton effect as a consequence of varying populations of two distinct polymer conformations. These two conformations are clearly visible in the N-15 NMR and IR spectra of the N-15-labeled poly(N-15-(1-naphthyl)-N'-octadecylcarbodiimide) (Poly-3) and poly(N-15-(1-naphthyl)-N-15'-octadecylcarbodiimide) (Poly-5). Using van't Hoff analysis, the enthalpies and entropies of switching (Delta H-switching; Delta S-switching) were calculated for both Poly-3 and Poly-5 using the relative integrations of both peaks in the N-15 NMR spectra at different temperatures to measure the populations of each state. The chiroptical switching (i.e., transitioning from state A to state B) was found to be an endothermic process (positive Delta H-switching) for both Poly-3 and Poly-5 in all solvents studied, meaning the conformation correlating with the downfield chemical shift (ca. 148 ppm, state B) is the higher enthalpy state. The compensating factor behind this phenomenon has been determined to be the large increase in entropy in CHCl3 as a result of the switching. Herein, we propose that the increased entropy in the system is a direct consequence of increased disorder in the solvent as the switching occurs. Specifically, the chloroform solvent molecules are very ordered around the polymer chains due to favorable solvent-polymer interactions, but as the switching occurs, these interactions become less favorable and disorder results. The same level of solvent disorder is not achieved in toluene, causing the chiroptical switching process to occur at higher temperatures.