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Halogenation of Alkenes02:46

Halogenation of Alkenes

15.6K
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.
15.6K
Alkyl Halides02:45

Alkyl Halides

16.6K
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...
16.6K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

2.5K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
2.5K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

8.1K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
8.1K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

12.9K
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.
12.9K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.0K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
6.0K

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Related Experiment Video

Updated: Jun 29, 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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A Halogen Bonding [2]Rotaxane Shuttle for Chloride-Selective Optical Sensing.

Hui Min Tay1, Andrew Docker1,2, Andrew J Taylor1

  • 1Department of Chemistry, University of Oxford Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 27, 2024
PubMed
Summary

This study introduces a novel rotaxane shuttle for selective optical sensing of chloride anions. The rotaxane

Keywords:
anion recognitionanti-Hofmeister selectivityhalogen bondingmechanically interlocked moleculesoptical sensing

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Area of Science:

  • Supramolecular Chemistry
  • Chemical Sensing
  • Molecular Machines

Background:

  • Rotaxanes are mechanically interlocked molecules with potential applications in molecular devices.
  • Selective anion sensing is crucial for environmental monitoring and biological studies.
  • Developing stimuli-responsive molecular systems remains a key challenge.

Purpose of the Study:

  • To report the first rotaxane shuttle for selective optical sensing of chloride anions.
  • To investigate the mechanism of anion-induced macrocycle translocation.
  • To demonstrate the potential of rotaxanes in selective chemical sensing.

Main Methods:

  • Synthesis of a rotaxane featuring naphthalene diimide (NDI) and halogen bonding (XB) stations.
  • Proton Nuclear Magnetic Resonance (NMR) spectroscopy to study molecular structure and interactions.
  • UV-Vis spectroscopy to monitor optical changes upon anion addition.
  • Chloride, bromide, and iodide anion titration experiments in aqueous-acetone.

Main Results:

  • The rotaxane selectively binds chloride anions over bromide and iodide.
  • Chloride ions induce macrocycle translocation to the XB station via halogen and hydrogen bonding.
  • Translocation is accompanied by a decrease in charge-transfer absorption.
  • Larger halide ions are sterically excluded from the binding site.

Conclusions:

  • The developed rotaxane shuttle demonstrates high selectivity for chloride detection.
  • Mechanical bond effects can be exploited for precise anion recognition.
  • This work presents a promising strategy for chloride-selective chemosensing in aqueous environments.