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Related Concept Videos

Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

10.7K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

12.8K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Halogenation of Alkenes02:46

Halogenation of Alkenes

21.6K
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.
21.6K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

15.3K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
15.3K
Alkyl Halides02:45

Alkyl Halides

22.9K
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...
22.9K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

4.0K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
4.0K

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Updated: Apr 18, 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

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Conversion Between 2- and 3-Dimensional Halogen-Bonded Networks Formed From a Single N-Oxide/Iodoalkyne Building

Jordan N Smith1, Courtney Ennis2, Huan V Doan1

  • 1Research School of Chemistry, Australian National University, Canberra, ACT, Australia.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 17, 2026
PubMed
Summary
This summary is machine-generated.

Researchers developed a new halogen-bonded framework that transforms from a 3D to a 2D structure upon solvent exchange. This study enhances understanding of dynamic porous materials and their activation processes.

Keywords:
N‐oxidecrystal engineeringhalogen bondporous networkself‐recognition

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Crystallography

Background:

  • Permanently porous halogen-bonded frameworks show promise but remain unrealized.
  • Understanding material behavior during activation (solvent exchange, vacuum) is limited.
  • Halogen bonding is a key interaction for designing porous materials.

Purpose of the Study:

  • To design and synthesize a novel halogen-bonded framework using a single building block.
  • To investigate the structural transformations of the framework upon solvent exchange.
  • To understand the role of halogen bonding in creating dynamic network materials.

Main Methods:

  • Solvent-dependent crystallization to control network formation.
  • Solvent exchange experiments to induce structural changes.
  • Synchrotron far-infrared spectroscopy to monitor phase transitions.

Main Results:

  • A 3D network assembled solely by halogen bonds was successfully generated.
  • The 3D network underwent a single-crystal transformation to a 2D phase upon solvent exchange.
  • Diagnostic spectroscopic signals for the phase transition were identified.

Conclusions:

  • Successfully created a dynamic halogen-bonded framework with a controllable 3D to 2D structural transformation.
  • Demonstrated the potential of halogen bonding for designing responsive porous materials.
  • Provided insights into the dynamic nature and activation mechanisms of halogen-bonded network materials.