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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

19.5K
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...
19.5K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

9.9K
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.
9.9K
Halogenation of Alkenes02:46

Halogenation of Alkenes

18.3K
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.
18.3K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

6.5K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
6.5K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

14.6K
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.
14.6K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.7K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
4.7K

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Updated: Jan 9, 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

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Anion-π catalysis with halogen bonding.

Bingqian Shi1, Qianmu Xu1, Kaiyang Fan1

  • 1Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling 712100, Shaanxi, P. R. China. xiang.zhang@nwafu.edu.cn.

Chemical Communications (Cambridge, England)
|December 2, 2025
PubMed
Summary
This summary is machine-generated.

Anion-π catalysis and halogen bonding synergistically improve decarboxylative Michael additions. This combined approach enhances reaction yield, selectivity, and resistance to interference compared to individual methods.

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Area of Science:

  • Organic chemistry
  • Catalysis

Background:

  • Halogen bonding is a non-covalent interaction involving an electrophilic region on the halogen atom of a Lewis acid and a nucleophilic region on a Lewis base.
  • Anion-π catalysis utilizes the electron-deficient π-system of aromatic compounds to activate anions.

Purpose of the Study:

  • To investigate the synergistic effects of anion-π catalysis and halogen bonding in decarboxylative Michael addition reactions.
  • To develop a more efficient and selective catalytic system for this important organic transformation.

Main Methods:

  • The study employed a combination of anion-π catalysts and halogen bonding interactions.
  • Decarboxylative Michael addition reactions were performed under various conditions to assess the catalytic performance.

Main Results:

  • The synergistic strategy significantly improved reaction yields compared to using either anion-π catalysis or halogen bonding alone.
  • Enhanced selectivity and anti-interference ability were observed, demonstrating the robustness of the combined approach.
  • The catalytic system proved effective for a range of substrates in decarboxylative Michael addition reactions.

Conclusions:

  • The combination of anion-π catalysis and halogen bonding offers a powerful synergistic approach for decarboxylative Michael addition reactions.
  • This strategy provides a valuable tool for organic synthesis, offering improved efficiency, selectivity, and stability.