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Related Concept Videos

Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.3K
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.
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Alkyl Halides02:45

Alkyl Halides

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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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Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

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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.
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Molecular Orbital Theory II

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Molecular Orbital Energy Diagrams
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Halogens03:01

Halogens

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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. 
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Covalent Bonding and Lewis Structures02:46

Covalent Bonding and Lewis Structures

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Compared to ionic bonds, which results from the transfer of electrons between metallic and nonmetallic atoms, covalent bonds result from the mutual attraction of atoms for a “shared” pair of electrons.
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Structure and Bonding of Halonium Compounds.

Juan D Velasquez1, Jorge Echeverría1, Santiago Alvarez2

  • 1Instituto de Síntesis Química y Catálisis Homogénea (ISQCH) and Departmento de Química Inorgánica, Facultad de Ciencias, Universidad de Zaragoza, Pedro Cerbuna 12, 50009 Zaragoza, Spain.

Inorganic Chemistry
|May 31, 2023
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Summary
This summary is machine-generated.

Researchers studied halonium compounds ([D···X···D]+) using structural and computational methods. They found these compounds have strong interactions, suggesting potential uses in catalysis and supramolecular chemistry.

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Area of Science:

  • Chemical bonding
  • Supramolecular chemistry
  • Halogen bonding

Background:

  • Halonium compounds ([D···X···D]+) are cationic species featuring a central halogen atom (X) bonded to two Lewis bases (D).
  • Understanding their geometrical parameters and bonding is crucial for predicting their reactivity and applications.

Purpose of the Study:

  • To investigate the geometrical parameters and bonding characteristics of [D···X···D]+ halonium compounds.
  • To explore the influence of halogen type (Cl, Br, I) and donor groups on the halonium framework and bond.
  • To elucidate the physical origin of the halonium interaction and its potential applications.

Main Methods:

  • Combined structural analysis using Cambridge Structural Database (CSD) searches.
  • Computational investigations employing density functional theory (DFT), molecular electrostatic potential (MEP), and energy decomposition analysis (EDA).

Main Results:

  • CSD searches revealed linear and symmetrical [D···X···D]+ frameworks with neutral donors.
  • DFT, MEP, and EDA analyses detailed the effects of varying halogen atoms and nitrogen-donor groups on the halonium structure and bond.
  • The interaction is attributed to a balance of electrostatic and orbital contributions (σ-hole bond), with interaction energies reaching 45 kcal/mol.

Conclusions:

  • Halonium bonds exhibit significant interaction strengths, arising from a combination of electrostatic and orbital factors.
  • These findings highlight the potential of halonium compounds as novel halonium transfer agents.
  • The study suggests applications in asymmetric halofunctionalization and as building blocks in supramolecular chemistry.