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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

5.5K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
5.5K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

4.3K
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.
4.3K
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

5.1K
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...
5.1K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.1K
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.
3.1K
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

2.3K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
2.3K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

3.8K
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...
3.8K

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Primary Pyrrolimines and Pyridinimines.

Amavi Kpoezoun1,2, Gnon Baba2, Jean-Claude Guillemin1

  • 1Univ Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)-UMR6226, F-35000 Rennes, France.

Molecules (Basel, Switzerland)
|March 27, 2025
PubMed
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Researchers synthesized novel imine compounds featuring pyrrole or pyridine rings. These kinetically unstable compounds present unique synthesis and isolation challenges due to their low volatility.

Keywords:
dehydrocyanationpyridiniminepyrrolimineretro-ene reaction

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Area of Science:

  • Organic Chemistry
  • Heterocyclic Chemistry

Background:

  • Aromatic imines are well-studied, particularly phenyl-substituted variants.
  • Recent advances include the synthesis of furan and thiophene substituted imines.

Purpose of the Study:

  • To synthesize and isolate novel N-unsubstituted imines directly linked to pyrrole or pyridine rings.
  • To investigate the physicochemical properties of these newly synthesized heterocyclic imines.

Main Methods:

  • Direct linkage of pyrrole or pyridine rings to N-unsubstituted aldimine or ketimine groups.
  • Characterization of synthesized compounds to determine their properties.

Main Results:

  • Successful synthesis of pyrrole and pyridine linked imines, expanding the known family of aromatic imines.
  • Observed lower volatility in pyrrole and pyridine derivatives compared to aryl, furan, or thiophene analogs.
  • Increased difficulty in synthesis and isolation due to kinetic instability and low volatility.

Conclusions:

  • This study expands the scope of known aromatic imines to include pyrrole and pyridine derivatives.
  • The inherent instability and low volatility of these compounds pose significant synthetic challenges.
  • Further research is needed to fully understand and utilize the physicochemical properties of these novel heterocyclic imines.