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Preparation of Amides01:29

Preparation of Amides

3.8K
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...
3.8K
Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

3.8K
One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
3.8K
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

4.2K
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...
4.2K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.9K
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...
3.9K
Nitriles to Carboxylic Acids: Hydrolysis01:08

Nitriles to Carboxylic Acids: Hydrolysis

4.8K
Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
4.8K
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

3.6K
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...
3.6K

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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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Selective Carboxylate Recognition Using Urea-Functionalized Unclosed Cryptands: Mild Synthesis and Complexation

Patryk Niedbała1, Maciej Majdecki1, Kajetan Dąbrowa1

  • 1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

The Journal of Organic Chemistry
|March 7, 2020
PubMed
Summary

Twelve new unclosed cryptand receptors were synthesized and show strong anion-binding capabilities, particularly for carboxylates, even in challenging mixed solvents. These novel receptors offer promising applications in anion recognition. Keywords: anion binding, cryptand receptors, carboxylate recognition, macrocyclic scaffold.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Host-Guest Chemistry

Background:

  • Development of novel receptors for selective anion recognition is crucial in various chemical and biological applications.
  • Macrocyclic compounds, particularly cryptands, offer unique three-dimensional binding pockets for guest molecules.
  • Understanding anion-host interactions is essential for designing efficient molecular recognition systems.

Purpose of the Study:

  • To synthesize and characterize a new series of unclosed cryptand receptors.
  • To evaluate the anion-binding properties of these novel receptors.
  • To investigate the selectivity of the receptors towards different anions, especially carboxylates, in competitive media.

Main Methods:

  • Synthesis of a stable 26-membered tetraamidic macrocyclic scaffold.
  • Introduction of various alkyl and aryl urea substituents via post-macrocyclization functionalization.
  • Evaluation of anion-binding properties using spectroscopic techniques in a DMSO-d6 + H2O (95:5 v/v) solvent mixture.

Main Results:

  • Successfully synthesized 12 new unclosed cryptand receptors with yields ranging from 65-98%.
  • Demonstrated strong binding affinities for anions, with a particular emphasis on carboxylates.
  • Observed robust anion-binding performance even in a highly competitive aqueous-organic solvent mixture.

Conclusions:

  • The newly developed unclosed cryptand receptors exhibit potent anion-binding capabilities.
  • The macrocyclic scaffold and urea substituents contribute to strong and selective carboxylate recognition.
  • These receptors represent a promising advancement in the field of anion sensing and separation.