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Related Concept Videos

Halogens03:01

Halogens

Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group.
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
Electrophiles02:28

Electrophiles

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...
Radical Halogenation: Thermodynamics01:34

Radical Halogenation: Thermodynamics

The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy between bonds broken and bonds...

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Updated: May 20, 2026

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

Published on: March 24, 2018

Electrochemistry of Hypervalent Halogen Compounds.

Igors Sokolovs1, Edgars Suna1, Robert Francke2

  • 1Latvian Institute for Organic Synthesis, Aizkraukles 21, Riga LV-1006, Latvia.

Accounts of Chemical Research
|May 19, 2026
PubMed
Summary

Electrochemical methods enable the in situ generation of hypervalent iodine(III) and bromine(III) compounds, offering safer alternatives to unstable reagents. This research details their synthesis, properties, and diverse applications in organic synthesis.

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Published on: November 22, 2016

Area of Science:

  • Synthetic Organic Chemistry
  • Electrochemistry
  • Halogen Chemistry

Background:

  • Hypervalent iodine(III) and bromine(III) compounds are valuable synthetic reagents.
  • Instability and handling risks limit the large-scale application of conventional hypervalent halogen compounds.
  • Electrochemical in situ generation offers a safer and more practical alternative.

Purpose of the Study:

  • To develop electrochemical methods for synthesizing hypervalent iodine and bromine species.
  • To explore the synthetic applications and reaction mechanisms of these electrochemically generated compounds.
  • To expand the scope of hypervalent halogen chemistry through novel synthetic routes.

Main Methods:

  • Anodic oxidation of iodoarenes in fluorinated alcohols (HFIP, TFE) for dialkoxy-λ3-iodanes.
  • Electrochemical synthesis of chelation-stabilized bromanes via anodic oxidation in HFIP.
  • Anodic oxidation in acetonitrile to generate iodonium salts.
  • Development of an acid-free method for anion-flexible iodonium salt synthesis.

Main Results:

  • Fluorinated dialkoxy-λ3-iodanes generated in situ are effective in oxidative coupling reactions.
  • Chelation-stabilized bromanes, particularly doubly chelated species, are isolable and exhibit tunable reactivity (ionic, SET, radical).
  • Diaryliodonium salts are accessible via a versatile, anion-flexible electrochemical method.
  • Access to hypervalent bromonium analogues remains challenging, limited to specific cyclic structures.

Conclusions:

  • Electrochemical synthesis provides a powerful platform for generating and utilizing hypervalent halogen reagents.
  • Novel hypervalent iodine and bromine species with diverse reactivity profiles have been developed.
  • These methods enhance safety and practicality, paving the way for broader applications in organic synthesis.