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Related Concept Videos

Hydrogen Bonds01:04

Hydrogen Bonds

12.7K
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...
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Hydrogen Bonds00:26

Hydrogen Bonds

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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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Dipole Moment of a Molecule
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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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Bond Polarity
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Atoms and molecules interact through bonds (or forces): intramolecular and intermolecular. The forces are electrostatic as they arise from interactions (attractive or repulsive) between charged species (permanent, partial, or temporary charges) and exist with varying strengths between ions, polar, nonpolar, and neutral molecules. The different types of intermolecular forces are ion–dipole, dipole–dipole, hydrogen bonds, and dispersion; among these, dipole–dipole, hydrogen...
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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

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"Anti-Electrostatic" Halogen Bonding.

Jana M Holthoff1, Elric Engelage1, Robert Weiss2

  • 1Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstraße 150, 44801, Bochum, Germany.

Angewandte Chemie (International Ed. in English)
|April 1, 2020
PubMed
Summary
This summary is machine-generated.

Researchers synthesized anionic organoiodine compounds that form counterintuitive "anti-electrostatic" halogen bonds (XBs) with anions. This study presents the first experimental examples of such interactions with organic XB donors and different anions.

Keywords:
density-functional calculationselectrostaticshalogen bondinghydrogen bondingnoncovalent interactions

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Area of Science:

  • Chemistry
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Halogen bonding (XB) is typically electrostatic, involving Lewis acids and bases.
  • Anionic XB donors forming XBs with anions appears counterintuitive due to electrostatic repulsion.
  • Previous experimental evidence for such "anti-electrostatic" XBs in organic systems was limited.

Purpose of the Study:

  • To synthesize and characterize novel negatively charged organoiodine compounds.
  • To experimentally demonstrate the formation of "anti-electrostatic" halogen bonds between anionic XB donors and anions.
  • To investigate the structural and energetic properties of these unique interactions.

Main Methods:

  • Synthesis of anionic organoiodine derivatives.
  • Density Functional Theory (DFT) calculations for electronic structure and stabilization.
  • X-ray crystallography for solid-state structure determination.
  • Co-crystallization experiments with various halide anions.

Main Results:

  • Successful synthesis of two negatively charged organoiodine compounds.
  • Experimental observation of self-association (dimers, trimers, chains) in the solid state.
  • Formation of co-crystals with halide anions, establishing the first "anti-electrostatic" XB adducts between organic anionic donors and different anions.
  • DFT calculations predicted kinetic stabilization of halide complexes, especially in solution.
  • Observed halogen bond lengths were significantly shorter (14-21%) than van der Waals radii sums.

Conclusions:

  • Demonstrated the feasibility of "anti-electrostatic" halogen bonding with organic anionic XB donors.
  • Provided the first experimental evidence for such interactions with different anions.
  • Highlighted the potential for kinetic stabilization in overcoming electrostatic barriers in halogen bonding.