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Halogenation of Alkenes02:46

Halogenation of Alkenes

21.7K
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.
21.7K
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...
2.4K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

4.1K
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
4.1K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

15.4K
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.
15.4K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

4.4K
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
4.4K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

5.3K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic...
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

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Solution and solid-phase halogen and C-H hydrogen bonding to perrhenate.

Casey J Massena1, Asia Marie S Riel, George F Neuhaus

  • 1Department of Chemistry, University of Montana, 32 Campus Dr., Missoula, MT 59812, USA. orion.berryman@umontana.edu.

Chemical Communications (Cambridge, England)
|December 16, 2014
PubMed
Summary

This study reveals strong halogen bonding in solution and bidentate association in the solid state between a pyridinium scaffold and perrhenate. A similar host molecule also showed significant C-H hydrogen bonding to perrhenate.

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Area of Science:

  • Supramolecular Chemistry
  • Crystal Engineering
  • Spectroscopy

Background:

  • Halogen bonding and hydrogen bonding are crucial non-covalent interactions in molecular recognition and self-assembly.
  • Pyridinium scaffolds offer versatile platforms for designing host molecules with specific binding properties.

Purpose of the Study:

  • To investigate the binding interactions between a 1,3-bis(4-ethynyl-3-iodopyridinium)benzene scaffold and perrhenate anions.
  • To explore the role of halogen bonding and hydrogen bonding in both solution and solid states.
  • To compare the binding behavior of a nearly isostructural host molecule.

Main Methods:

  • Proton Nuclear Magnetic Resonance ((1)H NMR) spectroscopy was employed to study interactions in solution.
  • X-ray crystallography was used to determine the solid-state structures and binding modes.
  • Comparative analysis of two host molecules with perrhenate was performed.

Main Results:

  • The primary scaffold exhibited strong halogen bonding interactions with perrhenate in solution.
  • In the solid state, the same scaffold demonstrated bidentate association with perrhenate.
  • A nearly isostructural host molecule showed significant C-H hydrogen bonding to perrhenate in both solution and solid phases.

Conclusions:

  • Halogen bonding and C-H hydrogen bonding are effective strategies for perrhenate recognition by tailored organic scaffolds.
  • The binding mode of the anion is influenced by the scaffold's structure and the phase (solution vs. solid state).
  • Structural modifications in host molecules can alter the dominant non-covalent interactions, leading to different binding behaviors.