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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
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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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Alkyl Halides02:45

Alkyl Halides

17.0K
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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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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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.
8.4K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.0K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.0K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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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.
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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Thiourea-Based Tritopic Halogen-Bonding Acceptors.

Lauri Happonen1, Milla Mattila1, Ivan Peshev1

  • 1Department of Chemistry, University of Jyvaskyla, Survontie 9 B, 40500, Jyväskylä.

Chemistry, an Asian Journal
|March 15, 2023
PubMed
Summary

Researchers synthesized novel thiourea-based receptors for halogen bonding. These molecules efficiently form halogen-bonded assemblies, demonstrating flexible sulfur acceptor properties in C-I⋅⋅⋅S bonds.

Keywords:
X-ray diffractionhalogen bondingisothiocyanates and thiocyanatesnoncovalent interactionsthiourea-based receptors

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Crystal Engineering

Background:

  • Thiourea derivatives serve as versatile building blocks in supramolecular chemistry.
  • Halogen bonding is a crucial non-covalent interaction for constructing ordered assemblies.
  • Developing efficient and safer synthetic routes for receptor molecules is essential.

Purpose of the Study:

  • To synthesize novel thiourea-based tritopic receptor molecules.
  • To investigate their utility as building blocks for halogen-bonded assemblies.
  • To explore the halogen-bond acceptor properties of the synthesized receptors.

Main Methods:

  • Synthesis of 16 new thiourea-based tritopic receptor molecules.
  • Utilized 2,4,6-trialkyl-1,3,5-tris(bromomethyl)benzene and tris(isothiocyanatomethyl)benzene intermediates.
  • Employed single-crystal X-ray diffraction to analyze halogen-bonded complexes.

Main Results:

  • Successfully synthesized 16 new receptor molecules via a safer route, avoiding toxic thiophosgene.
  • Obtained five new crystal structures of halogen-bonded complexes.
  • Receptors demonstrated the formation of two to four C-I⋅⋅⋅S halogen bonds with diiodotetrafluorobenzene donors.
  • Observed highly directional halogen bonds with flexible C=S⋅⋅⋅I acceptor angles.

Conclusions:

  • The synthesized thiourea-based receptors are effective building blocks for halogen-bonded assemblies.
  • The sulfur atoms in the receptors exhibit flexible halogen-bond acceptor capabilities.
  • The developed synthetic strategy offers a safer alternative for preparing such molecules.