4-氯苯胺-¹⁵N | 24176-54-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯苯胺-¹⁵N
• 英文名称: 4-chloroaniline-15N
• 英文别名: <15N>p-chloroaniline；p-Chloranilin-15N；4-Chlor-<15N>anilin；4-Chlor-(¹⁵N)anilin；4-chloro-[¹⁵N]aniline；(¹⁵N)-p-Chlor-anilin；4-chloro(15N)aniline
• CAS: 24176-54-3
• 化学式: C₆H₆ClN
• 分子量: 128.567
• InChiKey: QSNSCYSYFYORTR-VJJZLTLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-氯苯胺-¹⁵N 以53%的产率得到
  参考文献：
  名称：

  SHINE, H. J.;RHEE, EUN, SOOK, J. LABELLED COMPOUNDS AND RADIOPHARM., 1984, 21, N 6, 569-573

  摘要：

  DOI：
• 作为产物：
  描述：

  p-Chlorbenzamid 在 氢氧化钾 、 溴 作用下， 以 水 为溶剂， 以66%的产率得到4-氯苯胺-¹⁵N
  参考文献：
  名称：

  Effect of molecular motion and solvent interactions on nitrogen-15 relaxation in anilines

  摘要：

  AbstractDipolar relaxation of 15N in anilines and anilinium ions is influenced by overall motion of the molecule, by rotation about the aryl–‐nitrogen bond, by inversion of the aniline nitrogen and by interactions of the NH2 or NH3+ group with the solvent. These factors are assessed by comparison of the 13C and 15N dipolar relaxation times as a function of para‐substitution on the aryl ring. In the anilines (solvent CDCl3), electron withdrawal brings about faster relative motion of the amine side‐chain, contrary to expectation from consideration of CN rotation but in agreement with the effects from nitrogen inversion. The 15N dipolar relaxation time correlates with the Hammett σp. For the anilinium ions (solvent Me2SO‐d6), there is no correlation with σp and no qualitative relationship with either CN rotation or N inversion. Nitrogen‐15 relaxation, corrected for overall motion as judged by ring 13C relaxation, correlates with the inductive parameter σI. Electron withdrawal through induction reduces hydrogen bonding and increases side‐chain mobility. For most of the anilines and for all of the anilinium ions, solvent interactions cause the nitrogen side‐chain to be less mobile than the aryl ring. Under these circumstances, the Woessner approach cannot be used to calculate barriers. The hydrogen bond donor properties of the anilines are reduced in the absence of electron‐donating substituents, and the first barriers to NH2 rotation/inversion were calculated by this procedure: aniline in CDCl3 3.5 kcal/mol, p‐chloroaniline in CDCl3 3.4 kcal/mol and p‐nitroaniline in acetone 3.8 kcal/mol.

  DOI：

  10.1002/mrc.1270220506

文献信息

• Catalyst-Free Decarboxylative Amination of Carboxylic Acids in Water Microdroplets
  作者：Yifan Meng、Elumalai Gnanamani、Richard N. Zare

  DOI：10.1021/jacs.2c12236

  日期：2023.1.11

  to form microdroplets whose chemical contents are analyzed mass spectrometrically. All intermediates and products are determined using mass spectrometry (MS) as well as in some cases tandem mass spectrometry (MS2). These results support the following reaction mechanism: NR2OH, formed via reaction of the amine with •OH, reacts with benzoic acid to form an isocyanate via a Lossen rearrangement. Hydrolysis

  先前的研究表明，羟基自由基可以在水微滴的水气表面形成。我们报告了使用原位生成的羟基自由基在一个步骤中进行有机转化，即通过脱羧从芳基酸以及氨和伯/仲胺形成苯胺。将苯甲酸和胺类溶解在水中，将溶液喷洒形成微滴，通过质谱分析其化学成分。所有中间体和产物均使用质谱法 (MS) 以及在某些情况下串联质谱法 (MS 2 ) 进行测定。这些结果支持以下反应机制：NR 2OH 由胺与•OH 反应形成，与苯甲酸反应通过Lossen 重排形成异氰酸酯。水解后释放出 CO 2，​​然后生成苯胺产品。值得注意的是，这种转化的范围包括各种胺和芳香酸，并使它们能够一步转化为苯胺和N-取代苯胺。此外，该反应在室温下发生，不需要金属催化剂或有机溶剂。
• Effect of molecular motion and solvent interactions on nitrogen-15 relaxation in anilines
  作者：Joseph B. Lambert、Daniel Stec

  DOI：10.1002/mrc.1270220506

  日期：1984.5

  AbstractDipolar relaxation of 15N in anilines and anilinium ions is influenced by overall motion of the molecule, by rotation about the aryl–‐nitrogen bond, by inversion of the aniline nitrogen and by interactions of the NH2 or NH3+ group with the solvent. These factors are assessed by comparison of the 13C and 15N dipolar relaxation times as a function of para‐substitution on the aryl ring. In the anilines (solvent CDCl3), electron withdrawal brings about faster relative motion of the amine side‐chain, contrary to expectation from consideration of CN rotation but in agreement with the effects from nitrogen inversion. The 15N dipolar relaxation time correlates with the Hammett σp. For the anilinium ions (solvent Me2SO‐d6), there is no correlation with σp and no qualitative relationship with either CN rotation or N inversion. Nitrogen‐15 relaxation, corrected for overall motion as judged by ring 13C relaxation, correlates with the inductive parameter σI. Electron withdrawal through induction reduces hydrogen bonding and increases side‐chain mobility. For most of the anilines and for all of the anilinium ions, solvent interactions cause the nitrogen side‐chain to be less mobile than the aryl ring. Under these circumstances, the Woessner approach cannot be used to calculate barriers. The hydrogen bond donor properties of the anilines are reduced in the absence of electron‐donating substituents, and the first barriers to NH2 rotation/inversion were calculated by this procedure: aniline in CDCl3 3.5 kcal/mol, p‐chloroaniline in CDCl3 3.4 kcal/mol and p‐nitroaniline in acetone 3.8 kcal/mol.
• Becker, Heinz G. O.; Pfeifer, Dietmar; Radeglia, Reiner, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 12, p. 1591 - 1597
  作者：Becker, Heinz G. O.、Pfeifer, Dietmar、Radeglia, Reiner

  DOI：——

  日期：——
• Albinati; Moriyama; Rüegger, Inorganic Chemistry, 1985, vol. 24, # 25, p. 4430 - 4433
  作者：Albinati、Moriyama、Rüegger、Pregosin、Togni

  DOI：——

  日期：——
• PALIJCHUK, YU. A.;KOZHUSHKO, B. N.;SHOKOL, V. A., ZH. OBSHCH. XIMII, 1982, 52, N 3, 566-573
  作者：PALIJCHUK, YU. A.、KOZHUSHKO, B. N.、SHOKOL, V. A.

  DOI：——

  日期：——