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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.9K
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.
8.9K
Alkyl Halides02:45

Alkyl Halides

17.8K
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...
17.8K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

3.0K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
3.0K
α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

α-Halogenation of Carboxylic Acid Derivatives: Overview

3.6K
Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the...
3.6K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.1K
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 halogen to form a...
4.1K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

10.5K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
10.5K

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Updated: Oct 17, 2025

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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Uracil Derivatives for Halogen-Bonded Cocrystals.

Mónica Benito1, Yannick Roselló2, Miquel Barceló-Oliver2

  • 1Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Campus UAB, 08193 Bellaterra, Spain.

International Journal of Molecular Sciences
|October 13, 2021
PubMed
Summary

Researchers developed a green method to create novel halogen-bonded cocrystals using uracil derivatives. These supramolecular solids, formed via halogen bonding, offer new possibilities for crystal engineering and material design.

Keywords:
DFTcocrystalcrystal engineeringmechanochemistrynoncovalent interactionsnucleobases

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Area of Science:

  • Supramolecular Chemistry
  • Crystal Engineering
  • Organic Solid-State Chemistry

Background:

  • Halogen bonding is an increasingly important non-covalent interaction for supramolecular assembly.
  • Uracil derivatives are versatile building blocks in supramolecular chemistry.
  • 1,2,4,5-tetrafluoro-3,6-diiodobenzene is a potent halogen bond donor.

Purpose of the Study:

  • To report the synthesis and characterization of three new halogen-bonded cocrystals.
  • To explore the use of a green and effective method for cocrystal formation.
  • To investigate the role of halogen bonding in crystal packing compared to hydrogen bonding.

Main Methods:

  • Solvent-drop grinding and solution crystallization techniques were employed.
  • Characterization included powder and single-crystal X-ray diffraction.
  • Fourier-transformed infrared spectroscopy and thermal analysis (TGA-DSC) were utilized.
  • Computational methods were applied to analyze crystal packing interactions.

Main Results:

  • Three novel cocrystals incorporating uracil derivatives and 1,2,4,5-tetrafluoro-3,6-diiodobenzene were successfully synthesized.
  • The crystal structures confirmed the formation of halogen bonds as primary interaction.
  • Both solvent-drop grinding and solution methods proved effective for cocrystal preparation.
  • Comparative analysis highlighted the significance of halogen bonds in the observed crystal architectures.

Conclusions:

  • The study demonstrates a green and efficient approach to constructing halogen-bonded cocrystals.
  • The synthesized cocrystals showcase the potential of halogen bonding in designing functional supramolecular materials.
  • Understanding the interplay between halogen and hydrogen bonds is crucial for precise crystal engineering.