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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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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...
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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.
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Extended halogen bonding between fully fluorinated aromatic molecules.

Shigeki Kawai1,2, Ali Sadeghi1,3, Feng Xu4

  • 1†Department of Physics, University of Basel, Klingelbergstrasse 82, CH-4056 Basel, Switzerland.

ACS Nano
|February 27, 2015
PubMed
Summary
This summary is machine-generated.

Fluorine atoms in aromatic molecules can form directional C-F···F bonds, similar to halogen bonds, overcoming electrostatic repulsion through dispersion forces. This study reveals novel bonding interactions in fluorinated compounds.

Keywords:
F−F contactatomic force microscopychemical structurehalogen bondingintermolecular interaction

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Computational Chemistry

Background:

  • Halogen bonding is a key noncovalent interaction involving a σ-hole on halogen atoms.
  • Fully fluorinated aromatics were thought incapable of forming halogen bonds due to the lack of a σ-hole.
  • Understanding intermolecular forces in fluorinated systems is crucial for materials design.

Purpose of the Study:

  • To investigate the atomic-scale interactions between fluorine atoms in fully fluoro-substituted aromatic molecules.
  • To determine if C-F···F contacts can form and under what conditions.
  • To elucidate the nature and driving forces behind these interactions.

Main Methods:

  • High-resolution force microscopy for atomic-scale imaging of in-plane F-F contacts.
  • Ab initio calculations to model the electronic structure and intermolecular forces.
  • Analysis of electrostatic potential and dispersion forces.

Main Results:

  • Attractive dispersion forces can overcome electrostatic repulsion between fluorine atoms.
  • Anisotropic negative electrostatic potential contributes to directional C-F···F bonding.
  • A unique "windmill" structure formed by three C-F···F bonds was observed.
  • These interactions exhibit similarities to traditional halogen bonding despite the absence of a σ-hole.

Conclusions:

  • Fluorine atoms in aromatic systems can engage in directional noncovalent interactions resembling halogen bonding.
  • Dispersion forces and anisotropic electrostatic potentials play critical roles in forming C-F···F bonds.
  • The findings challenge the conventional understanding of halogen bonding and open new avenues for designing fluorinated materials.