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Related Concept Videos

Halogens03:01

Halogens

23.7K
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. 
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Alkyl Halides02:45

Alkyl Halides

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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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Halogenation of Alkenes02:46

Halogenation of Alkenes

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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.
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Radical Halogenation: Thermodynamics01:34

Radical Halogenation: Thermodynamics

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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...
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Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

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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.
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Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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Related Experiment Video

Updated: Feb 17, 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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Probing halogen-halogen interactions in solution.

V Ayzac1, M Raynal, B Isare

  • 1Sorbonne Universités, UPMC Univ Paris 06, CNRS, Institut Parisien de Chimie Moléculaire, Equipe Chimie des Polymères, 4 Place Jussieu, F-75005 Paris, France. laurent.bouteiller@upmc.fr.

Physical Chemistry Chemical Physics : PCCP
|November 30, 2017
PubMed
Summary
This summary is machine-generated.

This study developed a supramolecular balance to detect weak bromine-bromine (BrBr) interactions in solution. These findings reveal that solvent interactions often overpower BrBr bonds in aromatic solvents like toluene.

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Area of Science:

  • Supramolecular Chemistry
  • Halogen Bonding
  • Crystal Engineering

Background:

  • Halogen-halogen interactions are crucial in crystal engineering but difficult to detect in solution due to their weak nature.
  • Understanding these interactions in solution is vital for designing novel molecular systems and materials.

Purpose of the Study:

  • To design and implement a sensitive supramolecular system for detecting weak bromine-bromine (BrBr) interactions in solution.
  • To quantify the strength of BrBr interactions in different solvent environments.

Main Methods:

  • Development of a supramolecular balance sensitive to weak intermolecular forces.
  • Experimental detection and characterization of BrBr interactions between CBr3 groups in solution.
  • Thermodynamic analysis to estimate the free energy of BrBr interactions in halogenoalkane solvents.

Main Results:

  • Successfully detected BrBr interactions in solution near room temperature using the designed supramolecular balance.
  • Estimated the free energy of BrBr halogen bond interactions in halogenoalkane solvents.
  • Demonstrated that in toluene solutions, interactions between bromine atoms and aromatic solvent groups are stronger than BrBr interactions.

Conclusions:

  • The developed supramolecular balance is effective for detecting and studying weak halogen-halogen interactions in solution.
  • Solvent effects play a significant role, with aromatic solvent interactions potentially masking or dominating weak intramolecular halogen bonds.