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

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

7.5K
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.
7.5K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.5K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
2.5K
Electrophiles02:28

Electrophiles

12.8K
This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
12.8K
pH Scale02:41

pH Scale

79.7K
Hydronium and hydroxide ions are present both in pure water and in all aqueous solutions, and their concentrations are inversely proportional as determined by the ion product of water (Kw). The concentrations of these ions in a solution are often critical determinants of the solution’s properties and the chemical behaviors of its other solutes. Two different solutions can differ in their hydronium or hydroxide ion concentrations by a million, billion, or even trillion times. A common means of...
79.7K
EDTA: Auxiliary Complexing Reagents01:26

EDTA: Auxiliary Complexing Reagents

1.4K
EDTA titrations are usually carried out in highly basic conditions, where the fully deprotonated form of EDTA, Y4−, actively complexes with the free metal ions in the solution. Several metal ions precipitate as hydrous oxide (hydroxides, oxides, or oxyhydroxides) under these conditions, lowering the concentration of free metal ions in the solution. For this reason, auxiliary complexing agents or ligands such as ammonia, tartrate, citrate, or triethanolamine are used in EDTA titrations to...
1.4K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

10.6K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
10.6K

You might also read

Related Articles

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

Sort by
Same author

Biocatalytic synthesis of ribonucleoside analogues using nucleoside transglycosylase-2.

Chemical science·2024
Same author

Activation of fluoride anion as nucleophile in water with data-guided surfactant selection.

Chemical science·2024
Same author

Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas.

Beilstein journal of organic chemistry·2024
Same author

Going Full Circle with Organocatalysis and Biocatalysis: The Latent Potential of Cofactor Mimics in Asymmetric Synthesis.

The Journal of organic chemistry·2023
Same author

Allophycocyanin A is a carbon dioxide receptor in the cyanobacterial phycobilisome.

Nature communications·2022
Same author

Evidence of Rate Limiting Proton Transfer in an S<sub>N</sub>Ar Aminolysis in Acetonitrile under Synthetically Relevant Conditions.

The Journal of organic chemistry·2021

Related Experiment Video

Updated: Jan 31, 2026

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
08:47

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

Published on: March 6, 2019

10.1K

A quantitative reactivity scale for electrophilic fluorinating reagents.

Neshat Rozatian1, Ian W Ashworth2, Graham Sandford1

  • 1Chemistry Department , Durham University , South Road , Durham , DH1 3LE , UK .

Chemical Science
|January 1, 2019
PubMed
Summary

This study establishes a quantitative reactivity scale for N-F fluorination agents, aiding reagent selection in chemical synthesis. The findings provide crucial data for optimizing electrophilic fluorination in drug discovery and research.

More Related Videos

Covalent Fragment Screening Using the Quantitative Irreversible Tethering Assay
06:17

Covalent Fragment Screening Using the Quantitative Irreversible Tethering Assay

Published on: February 28, 2025

1.2K
A Strategy for Sensitive, Large Scale Quantitative Metabolomics
14:18

A Strategy for Sensitive, Large Scale Quantitative Metabolomics

Published on: May 27, 2014

21.7K

Related Experiment Videos

Last Updated: Jan 31, 2026

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
08:47

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

Published on: March 6, 2019

10.1K
Covalent Fragment Screening Using the Quantitative Irreversible Tethering Assay
06:17

Covalent Fragment Screening Using the Quantitative Irreversible Tethering Assay

Published on: February 28, 2025

1.2K
A Strategy for Sensitive, Large Scale Quantitative Metabolomics
14:18

A Strategy for Sensitive, Large Scale Quantitative Metabolomics

Published on: May 27, 2014

21.7K

Area of Science:

  • Organic Chemistry
  • Fluorination Chemistry

Background:

  • Electrophilic N-F fluorination is vital for introducing fluorine into aliphatic compounds for drug discovery.
  • Current N-F reagent selection relies on empirical methods due to a lack of quantitative electrophilicity data.

Purpose of the Study:

  • To establish an experimentally determined kinetic reactivity scale for ten N-F fluorinating reagents.
  • To provide quantitative data for selecting appropriate N-F reagents in synthetic chemistry.

Main Methods:

  • A kinetic reactivity scale was developed using ten N-F fluorinating reagents in acetonitrile (CH3CN).
  • Para-substituted 1,3-diaryl-1,3-dicarbonyl derivatives were employed to measure relative and absolute rate constants.
  • A spectrophotometric method was utilized to report reactivity.

Main Results:

  • A reactivity scale spanning eight orders of magnitude was established for the tested N-F reagents.
  • The study quantified the electrophilicities of Selectfluor™, NFSI, Synfluor™, and N-fluoropyridinium salts.
  • A novel form of tautomeric polymorphism was discovered using the dicarbonyl scaffold.

Conclusions:

  • The developed reactivity scale offers a quantitative basis for N-F fluorination reagent selection.
  • This work enhances the predictability and efficiency of electrophilic fluorination in organic synthesis.
  • The findings facilitate optimized fluorine incorporation in pharmaceutical research and development.