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Related Concept Videos

Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

10.3K
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.
10.3K
Halogenation of Alkenes02:46

Halogenation of Alkenes

16.6K
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.
16.6K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

2.9K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.9K
Hess's Law03:40

Hess's Law

46.9K
There are two ways to determine the amount of heat involved in a chemical change: measure it experimentally, or calculate it from other experimentally determined enthalpy changes. Some reactions are difficult, if not impossible, to investigate and make accurate measurements for experimentally. And even when a reaction is not hard to perform or measure, it is convenient to be able to determine the heat involved in a reaction without having to perform an experiment.
46.9K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

5.9K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
5.9K
Radical Halogenation: Thermodynamics01:34

Radical Halogenation: Thermodynamics

4.0K
The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy...
4.0K

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Related Experiment Video

Updated: Sep 25, 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

Published on: March 24, 2018

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Dual External Field-Engineered Hyperhalogen.

Xiao-Xiao Dong1, Yang Zhao1, Jun Li1

  • 1School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China.

The Journal of Physical Chemistry Letters
|April 27, 2022
PubMed
Summary
This summary is machine-generated.

Researchers developed a dual external field strategy to create hyperhalogens, superatoms with high electron affinity useful for superoxidizers. This method enhances cluster stability and precisely controls electron affinity for broader applications.

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Non-equilibrium Microwave Plasma for Efficient High Temperature Chemistry
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Quantification of Hydrogen Concentrations in Surface and Interface Layers and Bulk Materials through Depth Profiling with Nuclear Reaction Analysis
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Area of Science:

  • Computational Chemistry
  • Materials Science
  • Nanotechnology

Background:

  • Hyperhalogens are superatoms with exceptionally high electron affinity (EA), crucial for synthesizing potent superoxidizers.
  • Current understanding and design strategies for creating hyperhalogens remain limited, hindering their practical application.
  • Electron affinity is a key property determining a material's potential as a superoxidizer.

Purpose of the Study:

  • To propose a novel Dual External Field (DEF) strategy for constructing hyperhalogens.
  • To investigate the impact of DEF on the electron affinity and stability of gold (Au₈) and silver (Ag₁₇) nanoclusters.
  • To demonstrate a method for precise control over hyperhalogen properties.

Main Methods:

  • A noninvasive Dual External Field (DEF) strategy was employed, combining ligand field effects and an oriented external electric field (OEEF).
  • Computational modeling was used to study the Au₈ nanocluster's electronic properties under DEF.
  • The strategy's reliability was validated using an experimentally synthesized Ag₁₇ nanocluster.

Main Results:

  • The DEF strategy successfully increased the electron affinity of the Au₈ cluster, forming a hyperhalogen.
  • Ligation enhanced the nanocluster's stability, while OEEF allowed for precise, continuous tuning of electron affinity.
  • The approach proved effective for both the model Au₈ system and the experimentally relevant Ag₁₇ nanocluster.

Conclusions:

  • The proposed DEF strategy offers a powerful new route for designing and synthesizing hyperhalogens.
  • This method enables fine-tuning of electron affinity, crucial for developing advanced superoxidizers.
  • The DEF strategy holds significant potential for advancing hyperhalogen synthesis and applications in condensed-phase materials.