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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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).
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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...
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...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

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Updated: Jul 1, 2026

Green Synthesis of Quinoline-Based Ionic Liquid
05:59

Green Synthesis of Quinoline-Based Ionic Liquid

Published on: September 27, 2024

Electroactive Imidazolium Ionic Liquids in Organic Synthesis.

Cristiana Margarita1, Fabrizio Vetica2, Marta Feroci1

  • 1Department of Basic and Applied Sciences for Engineering (SBAI), Sapienza University of Rome, via Castro Laurenziano 7, 00161 Rome, Italy.

Accounts of Chemical Research
|June 29, 2026
PubMed
Summary

Electrochemistry combined with electroactive imidazolium-based ionic liquids (ILs) offers new synthetic pathways. This approach enables the electrogeneration of Lewis acids (LAs) and N-heterocyclic carbenes (NHCs) for efficient organic synthesis.

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Green Synthesis of Quinoline-Based Ionic Liquid
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Published on: September 27, 2024

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Area of Science:

  • Electrochemistry
  • Organic Synthesis
  • Ionic Liquids

Background:

  • Ionic liquids (ILs) are gaining attention in organic synthesis due to their unique properties like low vapor pressure and high stability.
  • Imidazolium-based ILs are particularly interesting as they can act as solvents, electrolytes, and precursors for reactive species.

Purpose of the Study:

  • To review recent advancements in using electroactive imidazolium-based ILs for organic synthesis.
  • To highlight the electrogeneration of Lewis acids (LAs) and N-heterocyclic carbenes (NHCs) using these ILs.
  • To critically assess electrochemical methods, setups, and their influence on reaction design and selectivity.

Main Methods:

  • Utilizing electroactive imidazolium-based ionic liquids as reaction media and precursors.
  • Employing electrochemical techniques for the generation of Lewis acids and N-heterocyclic carbenes.
  • Comparing electrochemically driven reactions with conventional synthetic methods.

Main Results:

  • Demonstrated successful electrogeneration of Lewis acids and N-heterocyclic carbenes from imidazolium-based ILs.
  • Showcased the versatility of these ILs in facilitating novel and efficient chemical transformations.
  • Highlighted improved reaction design and selectivity through electrochemical control.

Conclusions:

  • The combination of electrochemistry and electroactive imidazolium-based ILs presents a powerful toolkit for modern organic synthesis.
  • This approach offers sustainable and efficient alternatives to traditional synthetic methodologies.
  • Future research directions lie in expanding the scope and applications of these electrochemically driven IL systems.