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Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Preparation of Amides01:29

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...

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Updated: Jul 8, 2026

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
07:02

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry

Published on: August 25, 2016

乙烯和二胺混合物中n-丁的结构:混合溶解对1,2-添加物对伊米因的影响.

Bo Qu1, David B Collum

  • 1Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.

Journal of the American Chemical Society
|July 20, 2006
PubMed
概括
此摘要是机器生成的。

在特定的溶剂混合物中,n-Butyllithium (n-BuLi) 形成稳定的二元体. 通过胺和以太溶剂的合作溶解影响了n-BuLi添加反应的立体化学.

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科学领域:

  • 有机金属化学 有机金属化学
  • 溶液状态化学 溶液状态化学
  • 反应机制的反应机制

背景情况:

  • 对于n-Butyllithium (n-BuLi) 的聚合状态和溶解对于其反应性至关重要.
  • 了解这些因素是控制核友添加反应中的立体化学的关键.

研究的目的:

  • 研究n-BuLi在各种二胺/二甲基乙烯溶剂混合物中的结构特征和反应性.
  • 阐明合作溶解在1,2-加法反应的立体化学结果中的作用.

主要方法:

  • 核磁共振 (NMR) 谱学用于结构赋值.
  • 动力学研究 (速率研究) 以了解反应机制.
  • 使用特定的溶剂系统:TMEDA/THF,TMCDA/THF,TMCDA/THP,以及TMEDA/Et2O.

主要成果:

  • 混合过N,N,N,N',N'-四甲基环二胺 (TMCDA) 与四胺 (THP) 和N,N,N',N'-四甲基乙烯二胺 (TMEDA) 与二乙烯 (Et2O) 的混合物提供干净的结构赋值和优良的结构控制.
  • 在n-BuLi添加反应的过渡结构中观察到涉及TMCDA和THP的合作溶解.
  • 对于1,2-添加到imines,观察到不同的立体化学反应,与不同的溶解机制相关联.

结论:

  • 特定的溶剂混合物可以精确控制n-BuLi二极体的结构.
  • 合作溶解在决定n-BuLi加法反应的立体化学路径方面发挥着重要作用.
  • 这些发现为设计立体选择性有机金属反应提供了洞察力.