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Related Concept Videos

Preparation of Amides01:29

Preparation of Amides

4.1K
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...
4.1K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

6.9K
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.
6.9K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

4.1K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
4.1K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.7K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.7K
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

8.6K
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...
8.6K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.7K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.7K

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Stable and ordered amide frameworks synthesised under reversible conditions which facilitate error checking.

David Stewart1, Dmytro Antypov1, Matthew S Dyer1

  • 1Department of Chemistry, University of Liverpool, Liverpool, L69 7ZD, UK.

Nature Communications
|October 26, 2017
PubMed
Summary

Researchers developed a new method to create ordered covalent amide frameworks (CAFs) from amorphous polymers. This approach uses high temperature and pressure to enable reversible amide bond formation, leading to stable, crystalline networks.

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Area of Science:

  • Materials Science
  • Polymer Chemistry
  • Crystallography

Background:

  • Covalent organic frameworks (COFs) offer tunable properties via isoreticular chemistry.
  • Irreversible bond formation in COFs leads to amorphous materials with defects.
  • Reversible chemistries are crucial for crystalline network formation but are underexplored for amide bonds.

Purpose of the Study:

  • To develop a method for synthesizing ordered covalent amide frameworks (CAFs).
  • To overcome challenges associated with irreversible amide bond formation in network polymers.
  • To create robust amide-based networks with tunable properties.

Main Methods:

  • Devitrification of amorphous polyamide network polymers.
  • Application of high-temperature and high-pressure reaction conditions.
  • Utilizing reversible amide bond chemistry for network crystallization.

Main Results:

  • Successfully synthesized two- and three-dimensional covalent amide frameworks (CAFs).
  • Achieved reversible amide bond formation under specific reaction conditions.
  • Demonstrated the development of crystalline order in amide networks.
  • Produced CAFs with high thermal and hydrolytic stability (acidic and basic conditions).

Conclusions:

  • High-temperature and high-pressure conditions enable reversible amide bond formation for ordered CAF synthesis.
  • This strategy allows for the direct synthesis of stable, crystalline amide networks.
  • The developed CAFs exhibit exceptional stability, broadening their potential applications.