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Related Concept Videos

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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Hydrogen Bonds00:26

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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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Basicity of Aliphatic Amines01:21

Basicity of Aliphatic Amines

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Amines can behave as Brønsted–Lowry bases by accepting a proton from the acid to form corresponding conjugate acids. Due to a lone pair of nonbonding electrons, aliphatic amines can also act as Lewis bases by forming a covalent bond with an electrophile.
To measure the basicity of amines, two conventions are generally used. The first defines Kb as the basicity constant for the deprotonation reaction of water by the amine, as presented in Figure 1. Conventionally, lower Kb indicates...
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Effect of Lone Pairs of Electrons on Molecule Geometry
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Intermolecular Forces03:13

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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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Related Experiment Video

Updated: May 6, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Hydrogen-bonding interactions in gas-phase polyether/ammonium ion complexes.

C C Liou1, H F Wu, J S Brodbelt

  • 1Department of Chemistry and Biochemistry, University of Texas, 78712-1167, Austin, TX.

Journal of the American Society for Mass Spectrometry
|November 14, 2013
PubMed
Summary
This summary is machine-generated.

Hydrogen bonds are key in host-guest chemistry. This study shows strongly bound crown ether/ammonium ion complexes can fragment via covalent bonds, unlike weakly bound ones.

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Area of Science:

  • Supramolecular Chemistry
  • Mass Spectrometry
  • Physical Organic Chemistry

Background:

  • Hydrogen bonds are crucial for selective complexation in host-guest chemistry.
  • Crown ethers and ammonium ions are model systems for studying host-guest interactions.
  • Gas-phase studies provide insights into non-covalent interactions without solvent effects.

Purpose of the Study:

  • To investigate the nature and strength of hydrogen-bonding interactions in gas-phase crown ether/ammonium ion complexes.
  • To differentiate between weak and strong hydrogen bonding based on dissociation pathways.
  • To explore the fragmentation patterns of these complexes under collisional activation.

Main Methods:

  • Generation of hydrogen-bonded crown ether/ammonium ion complexes in the gas phase via association reactions.
  • Stabilization of complexes using collisions in a triple quadrupole mass spectrometer or quadrupole ion trap.
  • Analysis of complex stability and dissociation pathways using collision-activated dissociation (CAD) mass spectrometry.

Main Results:

  • Weakly bound complexes dissociate primarily through cleavage of hydrogen bonds, yielding intact protonated polyethers and/or ammonium ions.
  • Strongly bound complexes, featuring multiple hydrogen bonds, undergo extensive covalent bond cleavage of the polyether backbone in addition to hydrogen bond dissociation.
  • Complexes with multiple hydrogen bonds exhibit dissociation behavior suggesting high binding energies and potential for subsequent fragmentation of the polyether skeleton.

Conclusions:

  • The extent of covalent bond cleavage in collision-activated dissociation serves as a reliable indicator of hydrogen bond strength in these complexes.
  • Strong hydrogen bonding in polyether/ammonium ion complexes can lead to significant internal energy accumulation and subsequent skeletal fragmentation.
  • Gas-phase mass spectrometry is a powerful tool for dissecting non-covalent interactions and characterizing complex stability.