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Related Concept Videos

ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

5.7K
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...
5.7K
Radical Halogenation: Thermodynamics01:34

Radical Halogenation: Thermodynamics

3.8K
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...
3.8K
Halogenation of Alkenes02:46

Halogenation of Alkenes

16.1K
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.
16.1K
Alkyl Halides02:45

Alkyl Halides

17.1K
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...
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Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

2.7K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
2.7K
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

3.8K
Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
3.8K

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Updated: Aug 8, 2025

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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Halogen⋯Halogen Interactions: Nature, Directionality and Applications.

Binoy K Saha1, Ragima V P Veluthaparambath1, Vibha Krishna G1

  • 1Department of Chemistry, Pondicherry University, Puducherry, 605014, India.

Chemistry, an Asian Journal
|March 3, 2023
PubMed
Summary
This summary is machine-generated.

Halogen bonding, crucial in crystal engineering, involves interactions between F, Cl, Br, and I. This review clarifies their nature, geometry, and applications in supramolecular chemistry.

Keywords:
Charge densityHalogen⋅⋅⋅halogen interactionsSelf-assemblyStatistical analysisSupramolecular chemistry

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Area of Science:

  • Crystal Engineering
  • Supramolecular Chemistry
  • Chemical Physics

Background:

  • Halogen bonding (halogen⋯halogen interactions) is a key non-covalent interaction in crystal engineering.
  • Significant debate exists regarding the precise nature and geometric preferences of these interactions.
  • The behavior of halogens (F, Cl, Br, I) can differ based on their position in the periodic table and the atoms they are bonded to.

Purpose of the Study:

  • To review and clarify the diverse types of halogen bonding, including homo-halogen⋯halogen, hetero-halogen⋯halogen, and halogen⋯halide interactions.
  • To discuss the factors influencing the nature and preferred geometries of these interactions.
  • To explore the interchangeability of halogen bonding motifs with other supramolecular synthons and functional groups.

Main Methods:

  • Literature review of existing studies on halogen bonding.
  • Analysis of crystallographic data and computational studies (implied).
  • Discussion of various interaction types and their characteristics.

Main Results:

  • Detailed examination of halogen⋯halogen and halogen⋯halide interactions, their natures, and geometries.
  • Identification of different interaction motifs and their prevalence.
  • Discussion on the interchangeability of halogen bonding with other interactions and functional groups.

Conclusions:

  • Halogen bonding is a versatile interaction with predictable geometric preferences.
  • Understanding these interactions is crucial for designing crystalline materials.
  • The review highlights successful applications of halogen bonding in various chemical contexts.