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

Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.2K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.2K
Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution01:17

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

3.5K
Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
3.5K
Carbocations02:10

Carbocations

12.0K
Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
12.0K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

6.0K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
6.0K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.2K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.2K
Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

Nucleophilic Addition to the Carbonyl Group: General Mechanism

6.5K
The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of the incoming nucleophile, the reaction occurs via different mechanistic pathways.
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the...
6.5K

You might also read

Related Articles

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

Sort by
Same author

Cyclooctadiene-derived cage-divergent synthesis of heteroadamantanes and alternative polycyclic systems.

Organic & biomolecular chemistry·2026
Same author

Ligand flexibility as a concept to unlock catalytic activity: acyclic carbenes for base-free transfer ruthenium hydrogenation catalysis.

Chemical science·2026
Same author

Method of precise optical crystal alignment by tilting the diamond anvil cell.

Journal of applied crystallography·2025
Same author

Multigram Synthesis of 3,3-Spiro-α-prolines.

The Journal of organic chemistry·2024
Same author

Synthesis of Fused sp<sup>3</sup>-Enriched Imidazoles.

ChemistryOpen·2024
Same author

Parallel Minisci Reaction of <i>gem</i>-Difluorocycloalkyl Building Blocks.

ACS organic & inorganic Au·2024

Related Experiment Video

Updated: Oct 10, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.1K

Latent Nucleophilic Carbenes.

Anatoliy Marchenko1, Georgyi Koidan1, Anastasiya Hurieva1

  • 1Department of Organophosphorus Chemistry, Institute of Organic Chemistry, Murmanska 5, Kyiv 02660, Ukraine.

The Journal of Organic Chemistry
|December 13, 2021
PubMed
Summary

Noncyclic formamidines can transform into highly reactive aminocarbenes. A synthesized silylformamidine acts as a stable, latent carbene source, enabling reactions like CH bond insertion.

More Related Videos

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
12:19

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

8.6K
Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
14:07

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

13.8K

Related Experiment Videos

Last Updated: Oct 10, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.1K
Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
12:19

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

8.6K
Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
14:07

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

13.8K

Area of Science:

  • Organic Chemistry
  • Computational Chemistry

Background:

  • Noncyclic formamidines are precursors to aminocarbenes.
  • Aminocarbenes are reactive intermediates in organic synthesis.

Purpose of the Study:

  • To investigate the thermal rearrangement of noncyclic formamidines into aminocarbenes.
  • To synthesize and characterize a silylformamidine as a latent carbene source.
  • To explore the reactivity of the generated carbene.

Main Methods:

  • Density Functional Theory (DFT) and ab initio calculations.
  • Synthesis of silylformamidine.
  • Experimental reaction studies with acetylenes, benzenes, and trifluoromethane.

Main Results:

  • Noncyclic formamidines rearrange to aminocarbenes under mild conditions.
  • Silylformamidine exhibits the lowest activation energy for this rearrangement.
  • The carbene readily inserts into sp, sp2, and sp3 CH bonds.
  • The carbene reacts with various functional groups, showing high trimethylsilyl group mobility.

Conclusions:

  • Silylformamidine serves as a stable, latent source of a reactive nucleophilic carbene.
  • This carbene can be prepared in bulk, stored, and utilized as needed.
  • Similar behavior is predicted for other silylated formamidines and related compounds.