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Related Concept Videos

Preparation of Amides01:29

Preparation of Amides

3.3K
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...
3.3K
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

2.0K
Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
2.0K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.8K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
2.8K
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

2.2K
The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
2.2K
Ion Exchange01:17

Ion Exchange

700
Ion exchange chromatography separates charged molecules from a solution by reversibly exchanging them with mobile, or 'active', ions associated with the oppositely charged stationary phase. This method can be used to separate ions, soften and deionize water, and purify solutions. The polymers comprising the ion-exchange column are high-molecular-weight and chemically stable polymers, crosslinked to be porous and essentially insoluble. They are also functionalized with either acidic or...
700
Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

5.3K
Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
5.3K

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Related Experiment Video

Updated: Oct 15, 2025

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Dynamic Polyamide Networks via Amide-Imide Exchange.

Yinjun Chen1, Huiyi Zhang1, Soumabrata Majumdar1

  • 1Department of Chemical Engineering & Chemistry, Institute for Complex Molecular Systems, Eindhoven University of Technology, 5600 MB Eindhoven, The Netherlands.

Macromolecules
|November 1, 2021
PubMed
Summary
This summary is machine-generated.

Dynamic covalent polymer networks utilize a reversible amide-imide equilibrium for enhanced processibility above 110°C. This breakthrough offers tunable properties for advanced material applications.

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Dynamic covalent networks offer a unique combination of thermoset and thermoplastic properties.
  • Exploiting reversible chemical equilibria is key to designing self-healing and reprocessable materials.
  • The amide-imide equilibrium presents a novel pathway for creating dynamic polymer networks.

Purpose of the Study:

  • To synthesize dynamic covalent polymer networks using the amide-imide equilibrium.
  • To investigate the temperature-dependent properties and reversibility of these networks.
  • To explore the potential of these materials in additive manufacturing.

Main Methods:

  • Synthesis of dynamic covalent networks from pyromellitic diimide and poly(tetrahydrofuran) diamines.
  • Nuclear Magnetic Resonance (NMR) spectroscopy to study model amide-imide equilibrium reactions.
  • Variable temperature infrared (IR) spectroscopy to analyze equilibrium shifts in the network.
  • Mechanical testing (tensile modulus, strain at break) at various temperatures.

Main Results:

  • Successfully synthesized dynamic covalent networks with tunable properties.
  • Demonstrated significant network dissociation and increased viscosity above ≈110 °C due to amide-imide equilibrium shift.
  • Achieved fully reversible mechanical properties and multiple reprocessing cycles without property degradation.
  • Networks exhibit elastic solid behavior at room temperature (2-10 MPa modulus) and viscoelastic behavior at elevated temperatures.

Conclusions:

  • The amide-imide equilibrium is an effective mechanism for creating highly processible dynamic covalent polymer networks.
  • These materials bridge the gap between thermosets and thermoplastics, offering reprocessability and tunable mechanical properties.
  • The reversible nature and processibility at elevated temperatures make these networks suitable for additive manufacturing techniques like selective laser sintering.