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Related Concept Videos

Halogens03:01

Halogens

23.4K
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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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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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Bond Energies and Bond Lengths02:49

Bond Energies and Bond Lengths

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Stable molecules exist because covalent bonds hold the atoms together. The strength of a covalent bond is measured by the energy required to break it, that is, the energy necessary to separate the bonded atoms. Separating any pair of bonded atoms requires energy — the stronger a bond, the greater the energy required to break it.
31.3K
Peptide Bonds02:43

Peptide Bonds

82.5K
A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...
82.5K
Multiple Halogenation of Methyl Ketones: Haloform Reaction01:28

Multiple Halogenation of Methyl Ketones: Haloform Reaction

2.9K
A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic...
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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-catalysed Nazarov cyclisation reaction.

Alexander Dreger1, Patrick Wonner1, Elric Engelage1

  • 1Department of Chemistry and Biochemistry, Ruhr-Universität Bochum, Universitätsstraße 150, 44801 Bochum, Germany. stefan.m.huber@rub.de.

Chemical Communications (Cambridge, England)
|June 28, 2019
PubMed
Summary

Highly organized dicationic halogen bond donors are essential catalysts for the Nazarov cyclisation reaction. A noncoordinating counterion is crucial for achieving high catalytic activity in this important organic synthesis transformation.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Reaction Mechanisms

Background:

  • The Nazarov cyclisation is a vital electrocyclic reaction for synthesizing cyclopentenones.
  • Developing efficient catalytic systems for Nazarov cyclisation remains a significant challenge in organic synthesis.

Purpose of the Study:

  • To screen various halogen bond donors as catalysts for the Nazarov cyclisation.
  • To identify key structural features of catalysts that enhance reaction activity.

Main Methods:

  • Screening of neutral, mono-, and dicationic halogen bond donors.
  • Evaluation of catalyst performance in the Nazarov cyclisation reaction.
  • Investigation of the role of catalyst preorganization and counterion effects.

Main Results:

  • Dicationic halogen bond donors showed superior catalytic activity compared to neutral and monocationic counterparts.
  • A highly preorganized dicationic catalyst was identified as particularly effective.
  • The use of a noncoordinating counterion was found to be essential for maximizing catalytic efficiency.

Conclusions:

  • Highly preorganized dicationic halogen bond donors represent a promising class of catalysts for the Nazarov cyclisation.
  • Catalyst structure, specifically preorganization and counterion choice, significantly impacts activity.
  • This work provides valuable insights for the rational design of novel catalysts for Nazarov cyclisation and related reactions.