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Related Concept Videos

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 BondsHydrogen 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...
Radical Formation: Abstraction00:47

Radical Formation: Abstraction

The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
Even though homolysis produces radicals, it is different from radical...
Hess's Law03:40

Hess's Law

There are two ways to determine the amount of heat involved in a chemical change: measure it experimentally, or calculate it from other experimentally determined enthalpy changes. Some reactions are difficult, if not impossible, to investigate and make accurate measurements for experimentally. And even when a reaction is not hard to perform or measure, it is convenient to be able to determine the heat involved in a reaction without having to perform an experiment.
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the surface of...

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Updated: Jun 26, 2026

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method
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Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method

Published on: July 19, 2019

Host-guest hydrogen atom transfer induced by electron capture.

Changtong Hao1, Frantisek Turecek

  • 1Department of Chemistry, University of Washington, Seattle, Washington, USA.

Journal of the American Society for Mass Spectrometry
|February 3, 2009
PubMed
Summary

Electron capture triggers an unusual hydrogen transfer in alkanediammonium-dibenzo-18-crown-6-ether complexes. This intramolecular process, dependent on alkane chain length, involves both hydrogen atoms and protons moving to the crown ether ligand.

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Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method
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Area of Science:

  • Supramolecular Chemistry
  • Physical Chemistry
  • Chemical Physics

Background:

  • Noncovalent complexes involving crown ethers and ammonium cations are crucial in host-guest chemistry.
  • Understanding electron-induced reactions in such systems is vital for molecular electronics and sensing.
  • Previous studies have not detailed intramolecular hydrogen transfer in these specific complexes.

Purpose of the Study:

  • To investigate the mechanism of charge reduction in alkanediammonium-dibenzo-18-crown-6-ether complexes.
  • To elucidate the nature of hydrogen migration following electron capture.
  • To explore the influence of the alkane chain length on the observed transfer phenomena.

Main Methods:

  • Electron capture experiments with deuterium-labeled alkanediammonium cations.
  • Spectroscopic analysis to identify reaction products.
  • Ab initio quantum chemical calculations to model complex structures and reaction pathways.

Main Results:

  • Observation of an unprecedented intramolecular tandem hydrogen atom and proton transfer upon electron capture.
  • Deuterium labeling confirmed hydrogen origin from ammonium groups.
  • The extent of double hydrogen transfer correlated with the alkane chain length.
  • Computational analysis provided structural insights into complexes and dissociation products.

Conclusions:

  • The study presents the first evidence of intra-complex hydrogen transfer in these systems.
  • The phenomenon is attributed to the unique electronic properties of the complexes and the high hydrogen atom affinity of the dibenzo-18-crown-6-ether ligand.
  • This finding offers new perspectives on electron-initiated reactions in supramolecular assemblies.