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Related Concept Videos

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.
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...
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...
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.

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Related Experiment Video

Updated: May 30, 2026

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

Halogen bond involving hypervalent halogen: CSD search and theoretical study.

Weizhou Wang1

  • 1College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, China. wzwanglab@yahoo.com

The Journal of Physical Chemistry. A
|July 21, 2011
PubMed
Summary

This study reveals that hypervalent halogens can act as electron acceptors in halogen bonds, challenging typical assumptions. Computational analysis indicates these bonds are primarily electrostatic but can be weaker than those with monovalent halogens.

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

Published on: February 15, 2016

Area of Science:

  • Crystallography
  • Computational Chemistry
  • Supramolecular Chemistry

Background:

  • Halogen bonds typically involve monovalent halogens acting as electrophiles.
  • The Cambridge Structure Database reveals over seventy structures with hypervalent halogens participating in halogen bonds as acceptors.
  • The nature and strength of these hypervalent halogen bonds require detailed investigation.

Purpose of the Study:

  • To investigate the nature of halogen bonds involving hypervalent halogens.
  • To compare the strength and characteristics of hypervalent halogen bonds with those involving monovalent halogens.
  • To elucidate the reasons behind the observed bonding characteristics and electron density transfer.

Main Methods:

  • Utilized the Cambridge Structure Database for structural analysis.
  • Employed various theoretical methods, including Hartree-Fock (HF) and Møller-Plesset perturbation theory (MP2), with different basis sets for computational investigations.
  • Applied "atoms in molecules" (AIM) theory and natural bond orbital (NBO) theory to analyze bonding characteristics and electron density transfer.

Main Results:

  • HF calculations suggest a significant electrostatic contribution to hypervalent halogen bonding.
  • MP2 methods with medium basis sets were insufficient to accurately predict the relative strengths of hypervalent versus monovalent halogen bonds.
  • Accurate computational results indicated that hypervalent halogen bonds can be weaker than monovalent ones, even when the hypervalent halogen is more positively charged.

Conclusions:

  • Hypervalent halogens can indeed act as halogen bond acceptors, expanding the known scope of halogen bonding.
  • The electrostatic nature of these interactions is confirmed, but their strength relative to monovalent halogen bonds is complex and context-dependent.
  • Further analysis using AIM and NBO theories provides insights into the bonding characteristics and electron dynamics of hypervalent halogen bonds.