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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...
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...
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.
Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

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

Amines to Amides: Acylation of Amines

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 amide...

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Mechanochemical Methods for Amide Bond Formation.

Tatsiana Nikonovich1, Christos M Chatzigiannis2, Corentin Bordier2

  • 1Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia.

Chemical Reviews
|May 20, 2026
PubMed
Summary
This summary is machine-generated.

Mechanochemistry offers greener, more practical synthetic organic chemistry methods. This review details mechanochemical amide bond formation, a key area with industrial relevance and scale-up potential.

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Area of Science:

  • Synthetic organic chemistry
  • Mechanochemistry
  • Green chemistry

Background:

  • Mechanochemical methodologies are revolutionizing synthetic organic chemistry.
  • Amide bond formation is a critical transformation with significant industrial relevance.
  • Mechanochemistry offers enhanced practicality and reduced environmental impact compared to traditional methods.

Purpose of the Study:

  • To provide a comprehensive review of mechanochemical methods for amide bond formation.
  • To cover literature from early contributions to the present (September 2025).
  • To offer practical guidance for process optimization and scale-up in mechanochemical synthesis.

Main Methods:

  • Review of key substrate classes and methodological strategies for amide bond formation.
  • Discussion of direct coupling of carboxylic acids/derivatives with amines.
  • Exploration of unconventional approaches including surrogates, redox chemistry, rearrangements, and transition metal-mediated reactions.

Main Results:

  • Amide bond formation is the most developed area in mechanochemical organic synthesis.
  • Mechanochemical methods demonstrate scalability and successful scale-up examples.
  • The review covers mechanoenzymatic transformations and stereochemistry preservation.

Conclusions:

  • Mechanochemistry presents a powerful and sustainable alternative for amide bond synthesis.
  • This review serves as a resource for academic and industrial chemists exploring mechanochemistry.
  • Further development is needed in unexplored areas and to address current limitations.