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Related Concept Videos

Valence Bond Theory02:45

Valence Bond Theory

Overview of Valence Bond Theory
Valence Bond Theory02:42

Valence Bond Theory

Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...
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.
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.
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...
Hybridization of Atomic Orbitals I03:24

Hybridization of Atomic Orbitals I

The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...

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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

An overview of halogen bonding.

Peter Politzer1, Pat Lane, Monica C Concha

  • 1Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA. ppolitze@uno.edu

Journal of Molecular Modeling
|October 3, 2006
PubMed
Summary

Halogen bonding (XB) is a noncovalent interaction involving halogen atoms like chlorine, bromine, and iodine. This interaction, driven by a positive electrostatic potential called a sigma-hole, is crucial in biological systems and crystal engineering.

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Area of Science:

  • Chemistry
  • Biochemistry
  • Crystallography

Background:

  • Halogen bonding (XB) is a significant noncovalent interaction.
  • Halogen atoms (Cl, Br, I) act as electrophiles in XB interactions.
  • The strength of XB interactions increases from Cl to Br to I.

Purpose of the Study:

  • To explain the mechanism of halogen bonding.
  • To investigate the factors influencing halogen bond strength.
  • To highlight the importance of halogen bonding in various scientific fields.

Main Methods:

  • Review of experimental evidence for halogen bonding.
  • Computational analysis of sigma-hole properties.
  • Calculation and discussion of XB interaction energies.

Main Results:

  • Halogen bonding is explained by the presence of a sigma-hole, a region of positive electrostatic potential on the halogen atom.
  • The sigma-hole's magnitude depends on the halogen atom's electronic environment and hybridization.
  • Fluorine atoms typically do not form halogen bonds due to their high electronegativity and hybridization.
  • Computed interaction energies quantify the strength of various halogen bonds.

Conclusions:

  • Halogen bonding is a well-established interaction with predictable strength trends.
  • The sigma-hole model provides a robust explanation for halogen bonding.
  • Halogen bonding plays a vital role in biological systems and crystal engineering.