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Related Concept Videos

Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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.
Coordination Compounds and Nomenclature02:54

Coordination Compounds and Nomenclature

In most main group element compounds, the valence electrons of the isolated atoms combine to form chemical bonds that satisfy the octet rule. For instance, the four valence electrons of carbon overlap with electrons from four hydrogen atoms to form CH4. The one valence electron leaves sodium and adds to the seven valence electrons of chlorine to form the ionic formula unit NaCl (Figure 1a). Transition metals do not normally bond in this fashion. They primarily form coordinate covalent bonds, a...
Alkyl Halides02:45

Alkyl Halides

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...
Halogens03:01

Halogens

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.
Halogenation of Alkenes02:46

Halogenation of Alkenes

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.
Structural Isomerism02:34

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can be...

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Related Experiment Video

Updated: May 30, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Au(CN)n complexes: superhalogens with pseudohalogen as building blocks.

Devleena Samanta1, Miao Miao Wu, Purusottam Jena

  • 1Department of Chemistry, Virginia Commonwealth University, Richmond, Virginia 23284, USA. dsamanta@vcu.edu

Inorganic Chemistry
|August 17, 2011
PubMed
Summary

Researchers explored new superhalogens using pseudohalogens like cyanide (CN). Gold-cyanide complexes show high electron detachment energies but lower stability compared to gold-fluoride superhalogens.

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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

Related Experiment Videos

Last Updated: May 30, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

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

Area of Science:

  • Computational chemistry
  • Materials science
  • Quantum chemistry

Background:

  • Electron affinity (EA) is crucial for chemical reactivity.
  • Superhalogens possess electron affinities exceeding that of chlorine (3.6 eV).
  • Conventional superhalogens often involve metal-halogen (MX) structures.

Purpose of the Study:

  • Investigate pseudohalogens, specifically cyanide (CN), as building blocks for novel superhalogens.
  • Explore the synthesis and stability of gold-cyanide (Au(CN)n) superhalogens.
  • Differentiate between electron affinity (EA) and adiabatic detachment energy (ADE).

Main Methods:

  • Density functional theory (DFT) calculations were employed.
  • Investigated the electronic properties and stability of Au(CN)n complexes.
  • Analyzed the structural and energetic differences between Au(CN)n and AuF(n) systems.

Main Results:

  • Superhalogens with electron detachment energies up to 8.4 eV were predicted for gold-cyanide (Au(CN)n) complexes.
  • Au(CN)n complexes exhibit significantly lower stability (metastable beyond n=1 for neutrals, n=3 for anions) than AuF(n) analogues.
  • Key differences in stability and electronic structure between pseudohalogen and halogen-based superhalogens were identified.

Conclusions:

  • Pseudohalogens like CN can form superhalogens with high electron detachment energies.
  • The stability of superhalogens is highly dependent on the nature of the ligand (e.g., CN vs. F).
  • Clarified the distinction between electron affinity (EA) and adiabatic detachment energy (ADE) in superhalogen research.