Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

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).
Preparation of Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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...
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
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.
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Ordered Ionic-Liquid Channels Enable Fast Anhydrous Proton Conduction at up to 240°C for Fuel Cells.

Angewandte Chemie (International ed. in English)·2026
Same author

Proton-shuttling nanosheet membranes enable high-power-density protonic fuel cells.

Science advances·2026
Same author

Mass-Transport Effects in the Lithium Redox-Mediated Nitrogen Reduction Reaction.

Journal of the American Chemical Society·2026
Same author

Implications of Structural Disorder for the Electrocatalytic Properties of MoS<sub>2</sub> Materials.

Journal of the American Chemical Society·2026
Same author

Electrochemistry of Organic and Organometallic Compounds.

Molecules (Basel, Switzerland)·2026
Same author

Electrochemical Choline Sensing: Biological Context, Electron Transfer Pathways and Practical Design Strategies.

Biomolecules·2026

Related Experiment Video

Updated: Jun 6, 2026

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

Nitrile functionalized methimazole-based ionic liquids.

Amal I Siriwardana1, Angel A J Torriero, Juan M Reyna-González

  • 1School of Chemistry, Monash University, Clayton, 3800, VIC, Australia. amal.siriwardana@monash.edu

The Journal of Organic Chemistry
|November 18, 2010
PubMed
Summary
This summary is machine-generated.

New room temperature ionic liquids were synthesized from methimazole derivatives. These novel ionic liquids demonstrate efficient extraction of silver ions from aqueous solutions, showcasing their potential in separation technologies.

More Related Videos

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
06:31

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

Green Synthesis of Quinoline-Based Ionic Liquid
05:59

Green Synthesis of Quinoline-Based Ionic Liquid

Published on: September 27, 2024

Related Experiment Videos

Last Updated: Jun 6, 2026

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

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
06:31

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

Green Synthesis of Quinoline-Based Ionic Liquid
05:59

Green Synthesis of Quinoline-Based Ionic Liquid

Published on: September 27, 2024

Area of Science:

  • Chemical synthesis
  • Materials science
  • Electrochemistry

Background:

  • Methimazole derivatives are known for their versatile chemical properties.
  • Ionic liquids offer unique advantages as solvents and electrolytes.
  • Developing new ionic liquids with specific functionalities is crucial for advanced applications.

Purpose of the Study:

  • To synthesize novel nitrile-functionalized methimazole-based room temperature ionic liquids.
  • To characterize the electrochemical properties of the synthesized ionic liquids.
  • To evaluate the efficiency of these ionic liquids for silver ion extraction.

Main Methods:

  • Alkylation of 2-mercapto-1-methylimidazole with chloroacetonitriles.
  • Anion metathesis using lithium bis(trifluoromethanesulfonyl)amide.
  • Electrochemical window determination.
  • Silver ion extraction experiments from aqueous media.

Main Results:

  • Successfully synthesized two nitrile-functionalized methimazole-based room temperature ionic liquids (3a and 3b) in high yields (94% and 89%).
  • The synthesized ionic liquids (3a and 3b) exhibit reasonably wide electrochemical windows.
  • Efficient extraction of Ag(+) from aqueous solutions into ionic liquids 3a and 3b was achieved.

Conclusions:

  • Nitrile-functionalized methimazole-based ionic liquids can be efficiently synthesized.
  • These novel ionic liquids possess suitable electrochemical properties for potential applications.
  • The developed ionic liquids are effective in the selective extraction of silver ions from aqueous media.