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Preparation of Amides01:29

Preparation of Amides

2.9K
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...
2.9K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.3K
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...
2.3K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

9.8K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
9.8K
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

2.0K
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
2.0K
Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

4.4K
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.
4.4K
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

3.0K
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
3.0K

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Using LDI-MS to Explore Amide Coupling Reactions with Carboxylate Terminated N-Heterocyclic Carbene Monolayers.

Lilian Chinenye Ekowo1, Nathaniel L Dominique1, Gurkiran Kaur2

  • 1Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States.

Journal of the American Society for Mass Spectrometry
|April 21, 2025
PubMed
Summary

N-Heterocyclic carbene (NHC) monolayers on gold show promise for biomolecule immobilization. Laser desorption/ionization mass spectrometry revealed NHC coupling is tolerant of steric bulk but requires esterification for amino acids like lysine.

Keywords:
N-heterocyclic carbene monolayersgold nanoparticleslaser desorption/ionization mass spectrometry

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Analysis of Complex Molecules and Their Reactions on Surfaces by Means of Cluster-Induced Desorption/Ionization Mass Spectrometry
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Area of Science:

  • Surface Chemistry
  • Biotechnology
  • Analytical Chemistry

Background:

  • N-Heterocyclic carbene (NHC) monolayers on gold are promising for biomolecule immobilization in biotechnology.
  • Amide linkage is the primary method for coupling carboxylic acid-functionalized NHCs with amine-terminated biomolecules.

Purpose of the Study:

  • To investigate the impact of steric bulk, ring strain, and amine substrate functionality on NHC-gold coupling reactions.
  • To explore the functional group tolerance of NHC monolayers for biomolecule immobilization.
  • To establish general principles for designing NHC-based biotechnology applications.

Main Methods:

  • Utilized a model system of carboxylic acid-terminated NHC-gold.
  • Employed laser desorption/ionization mass spectrometry (LDI-MS) to monitor amide linkage products.
  • Screened a range of amine substrates with varying steric bulk and ring strain.

Main Results:

  • NHC monolayers demonstrated successful coupling with a wide array of amine substrates, contrary to expectations for sterically hindered ones.
  • Coupling of l-lysine, a model biomolecule, was not observed.
  • NHC coupling reactions are intolerant to bifunctional amines with terminal carboxylic acids; esterification is necessary for amino acid coupling.

Conclusions:

  • NHC monolayers offer a versatile platform for biomolecule immobilization, accommodating diverse amine substrates.
  • Functional group tolerance is a critical factor, with esterification being essential for successful amino acid conjugation.
  • These findings provide a guide for optimizing NHC-based surface functionalization in biotechnological applications.