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Related Concept Videos

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...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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.
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
Hydrogen Bonds01:04

Hydrogen Bonds

A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
Hydrogen Bonds00:26

Hydrogen Bonds

Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared.

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Updated: May 29, 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 bonding interaction between fluorohalides and isocyanides.

Linda J McAllister1, Duncan W Bruce, Peter B Karadakov

  • 1Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.

The Journal of Physical Chemistry. A
|September 6, 2011
PubMed
Summary
This summary is machine-generated.

This study reveals that chlorine forms varied halogen bonds with isocyanides, unlike bromine and iodine. Incorporating basis set superposition error (BSSE) corrections refines geometric analyses and correlation models for these interactions.

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Area of Science:

  • Computational Chemistry
  • Quantum Chemistry
  • Molecular Interactions

Background:

  • Halogen bonding is a significant non-covalent interaction.
  • Understanding halogen bond characteristics is crucial for molecular recognition and materials science.
  • The Steiner-Limbach relationship provides a framework for analyzing halogen bond geometries.

Purpose of the Study:

  • To investigate the binding energies and optimized geometries of complexes formed between fluorohalides (FX) and various isocyanides (CNY).
  • To analyze the influence of basis set superposition error (BSSE) on geometric optimizations and correlations.
  • To explore the applicability and refinement of the Steiner-Limbach relationship for describing halogen bonding.

Main Methods:

  • High-level ab initio calculations using the MP2(Full)/aug-cc-pVTZ level of theory.
  • Basis set superposition error (BSSE) corrections were applied using the counterpoise (CP) method.
  • Analysis of optimized geometries using the standard and an extended four-parameter Steiner-Limbach relationship.

Main Results:

  • Optimized geometries and binding energies were determined for numerous fluorohalide-isocyanide complexes.
  • BSSE corrections significantly improved the correlations derived from the Steiner-Limbach relationship.
  • An extended Steiner-Limbach relationship provided further enhancements in correlation analysis.
  • Chlorine exhibited varied halogen bond types dependent on isocyanide basicity, unlike bromine and iodine.

Conclusions:

  • The study highlights the importance of BSSE corrections in accurately describing halogen bonding.
  • The refined Steiner-Limbach relationship offers a more comprehensive model for halogen bond geometry analysis.
  • Differential behavior of halogen bond donors (Cl vs. Br/I) was observed, influenced by electronic factors and geometric parameters.