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Related Concept Videos

Hydrogen Bonds00:26

Hydrogen Bonds

131.9K
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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Hydrogen Bonds01:04

Hydrogen Bonds

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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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IR Spectrum Peak Broadening: Hydrogen Bonding01:23

IR Spectrum Peak Broadening: Hydrogen Bonding

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The vibrational frequency of a bond is directly proportional to its bond strength. As a result, stronger bonds vibrate at higher frequencies, while weaker bonds vibrate at lower frequencies. The stretching vibration of the strong O–H bond in alcohols and phenols (very dilute solution or gas phase) appears as a sharp peak at 3600–3650 cm−1.
However, the extent of hydrogen bonding influences the observed stretching frequency and band broadening. Intermolecular or intramolecular...
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Valence Bond Theory02:45

Valence Bond Theory

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Overview of Valence Bond Theory
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Covalent Bonds01:29

Covalent Bonds

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Ionic Bonds00:42

Ionic Bonds

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Overview
When atoms gain or lose electrons to achieve a more stable electron configuration they form ions. Ionic bonds are electrostatic attractions between ions with opposite charges. Ionic compounds are rigid and brittle when solid and may dissociate into their constituent ions in water. Covalent compounds, by contrast, remain intact unless a chemical reaction breaks them.
Opposing Charges Hold Ions Together in Ionic Compounds
Ionic bonds are reversible electrostatic interactions between ions...
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Hydrogen Production and Utilization in a Membrane Reactor
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Chloride capture using a C-H hydrogen-bonding cage.

Yun Liu1, Wei Zhao1, Chun-Hsing Chen1

  • 1Department of Chemistry, Indiana University, Bloomington, IN 47405, USA.

Science (New York, N.Y.)
|May 25, 2019
PubMed
Summary

Researchers developed a novel synthetic receptor using only carbon-hydrogen (CH) bonds for highly selective chloride recognition. This cage receptor exhibits attomolar affinity, challenging traditional designs based on OH and NH hydrogen bonding.

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Area of Science:

  • Supramolecular Chemistry
  • Synthetic Receptor Design
  • Anion Recognition

Background:

  • Biomolecular recognition typically relies on OH and NH hydrogen bonds for tight binding and selectivity.
  • Synthetic receptors have largely mimicked these natural interactions.
  • Achieving high affinity and selectivity with alternative bonding motifs remains a challenge.

Purpose of the Study:

  • To design and synthesize a novel synthetic receptor capable of highly selective anion binding.
  • To investigate the potential of carbon-hydrogen (CH) hydrogen bonding in receptor design.
  • To demonstrate attomolar affinity and selectivity for chloride ions using a CH-bonding-based receptor.

Main Methods:

  • Design and synthesis of a cryptand-like cage receptor incorporating 1,2,3-triazole units.
  • X-ray crystallography to elucidate the binding mode and interactions.
  • Liquid-liquid extraction experiments to quantify binding affinity and selectivity.
  • Control experiments to validate the role of structural rigidity and CH hydrogen bonding.

Main Results:

  • A novel cage receptor was synthesized, utilizing six 1,2,3-triazole units for chloride binding.
  • Crystallography confirmed chloride stabilization via six short (2.7 Å) CH hydrogen bonds.
  • Attomolar affinity (10^-17 M) for chloride was achieved in liquid-liquid extractions.
  • Demonstrated high selectivity for chloride over other anions (Cl⁻ > Br⁻ > NO₃⁻ > I⁻) and anti-Hofmeister behavior.

Conclusions:

  • CH hydrogen bonding can effectively mediate tight binding and high selectivity in synthetic receptors.
  • The designed cage receptor represents a significant advancement in anion recognition, challenging conventional design principles.
  • The receptor shows potential applications in areas such as anti-Hofmeister salt extraction and corrosion inhibition.