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Related Concept Videos

Halogens03:01

Halogens

18.5K
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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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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Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

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sp3d and sp3d 2 Hybridization
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Exceptions to the Octet Rule02:55

Exceptions to the Octet Rule

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Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:
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Halogenation of Alkenes02:46

Halogenation of Alkenes

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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.
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Ionic Bonding and Electron Transfer02:48

Ionic Bonding and Electron Transfer

41.6K
Ions are atoms or molecules bearing an electrical charge. A cation (a positive ion) forms when a neutral atom loses one or more electrons from its valence shell, and an anion (a negative ion) forms when a neutral atom gains one or more electrons in its valence shell. Compounds composed of ions are called ionic compounds (or salts), and their constituent ions are held together by ionic bonds: electrostatic forces of attraction between oppositely charged cations and anions. 
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Updated: Jul 12, 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

69.1K

The Tetrel Bonds of Hypervalent Halogen Compounds.

Zhihao Niu1, Sean A C McDowell2, Qingzhong Li1

  • 1The Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China.

Molecules (Basel, Switzerland)
|October 28, 2023
PubMed
Summary

This study explores tetrel bonds in molecules with carbon and silicon. Tetrel bond strength is influenced by halogen electronegativity, with silicon-based compounds showing significantly enhanced interactions.

Keywords:
group transferhypervalent halogentetrel bondσ-hole

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Area of Science:

  • Computational chemistry
  • Quantum chemistry
  • Supramolecular chemistry

Background:

  • Tetrel bonds are non-covalent interactions involving Group 14 elements.
  • Understanding tetrel bond characteristics is crucial for designing novel materials and catalysts.
  • The influence of halogen substituents on tetrel bond strength requires further investigation.

Purpose of the Study:

  • To investigate the tetrel bond between PhXF2Y(TF3) and MCN electron donors.
  • To analyze the effect of halogen electronegativity on tetrel bond strength.
  • To explore the enhancement of tetrel bonds involving silicon.

Main Methods:

  • Density functional theory (DFT) calculations using the M06-2X functional.
  • Basis set employed: aug-cc-pVDZ.
  • Systematic variation of halogen substituents (X and Y) and metal centers (M).

Main Results:

  • Tetrel bond strength increases with the electronegativity of halogen X but decreases with the electronegativity of halogen Y.
  • Most carbon-based complexes exhibited interaction energies below 10 kcal/mol.
  • Silicon-based complexes showed significantly enhanced tetrel bonds (up to ~100 kcal/mol) with covalent Si-N interactions, inversion, and potential transfer.

Conclusions:

  • The nature and position of halogen substituents critically influence tetrel bond strength.
  • Silicon-based tetrel bonds are considerably stronger than their carbon counterparts, exhibiting covalent character.
  • These findings provide insights into the factors governing non-covalent interactions and their potential applications.