Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

π Molecular Orbitals of the Allyl Radical01:27

π Molecular Orbitals of the Allyl Radical

4.6K
Allyl radicals are three-carbon conjugated systems. They are readily formed as intermediates in halogenation reactions of alkenes involving the addition of halogen to the allylic carbon instead of the double bond. As seen in allyl cations and anions, each of the three sp2-hybridized carbon atoms in allyl radicals has an unhybridized p orbital. These orbitals combine to give three π molecular orbitals.
The allyl systems have identical molecular orbitals but differ in the number of π electrons....
4.6K
Ionic Bonds00:42

Ionic Bonds

131.3K
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...
131.3K
Bond Energies and Bond Lengths02:49

Bond Energies and Bond Lengths

31.5K
Stable molecules exist because covalent bonds hold the atoms together. The strength of a covalent bond is measured by the energy required to break it, that is, the energy necessary to separate the bonded atoms. Separating any pair of bonded atoms requires energy — the stronger a bond, the greater the energy required to break it.
31.5K
Osmosis and Osmotic Pressure of Solutions02:40

Osmosis and Osmotic Pressure of Solutions

46.7K
A number of natural and synthetic materials exhibit selective permeation, meaning that only molecules or ions of a certain size, shape, polarity, charge, and so forth, are capable of passing through (permeating) the material. Biological cell membranes provide elegant examples of selective permeation in nature, while dialysis tubing used to remove metabolic wastes from blood is a more simplistic technological example. Regardless of how they may be fabricated, these materials are generally...
46.7K
Covalent Bonds01:29

Covalent Bonds

163.2K
Overview
163.2K
Peptide Bonds02:43

Peptide Bonds

83.3K
A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...
83.3K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Spin-lattice relaxation of copper and vanadyl porphyrins in extended molecular framework materials.

Dalton transactions (Cambridge, England : 2003)·2026
Same author

Direct Energy Gap Calculations in Heisenberg Spin Systems Using Superconducting Quantum Devices.

Journal of computational chemistry·2026
Same author

An efficient 2,6-di(thiazol-2-yl)pyridine-based chemosensor for dual-response fluorometric and colorimetric detection of Fe<sup>2+</sup> and Cu<sup>2</sup>.

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy·2026
Same author

Hydrosilafluorenes as Recyclable Coupling Reagents for Direct Amidation of Carboxylic Acids with Amines.

Organic letters·2025
Same author

Magnetic Dynamics and Elongated Coherence of a High-Spin Mn(II) Qubit Doped Into a Metal-Organic Framework.

Chemistry (Weinheim an der Bergstrasse, Germany)·2025
Same author

Hamiltonian simulation-based quantum-selected configuration interaction for large-scale electronic structure calculations with a quantum computer.

Physical chemistry chemical physics : PCCP·2025

Related Experiment Video

Updated: Feb 7, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.7K

Reversible Solution π-Dimerization and Long Multicenter Bonding in a Stable Phenoxyl Radical.

Nico M Bonanno1, Prashanth K Poddutoori2, Kazunobu Sato3

  • 1Department of Chemistry, Brock University, 1812 Sir Isaac Brock Way, St.Catharines, Ontario, L2S3A1, Canada.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 25, 2018
PubMed
Summary

Stable phenoxyl radicals exhibit reversible π-dimerization in solution. This unique behavior, observed in 2,6-bis-(8-quinolylamino)-4-(tert-butyl)phenoxyl (BAQP), involves multicenter bonding and is supported by theoretical calculations.

Keywords:
density functional calculationsmolecular devicesmulticenter bondingstable radicalsπ-dimerization

More Related Videos

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

20.8K
Chemical Dimerization-Induced Protein Condensates on Telomeres
08:52

Chemical Dimerization-Induced Protein Condensates on Telomeres

Published on: April 12, 2021

3.7K

Related Experiment Videos

Last Updated: Feb 7, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.7K
Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

20.8K
Chemical Dimerization-Induced Protein Condensates on Telomeres
08:52

Chemical Dimerization-Induced Protein Condensates on Telomeres

Published on: April 12, 2021

3.7K

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Computational Chemistry

Background:

  • Phenoxyl radicals are known for their stability and diverse chemical reactivity.
  • π-dimerization is a common phenomenon in aromatic systems, influencing their electronic and structural properties.
  • Previous studies on phenoxyl radicals have not reported reversible π-dimerization in solution.

Purpose of the Study:

  • To investigate the phenomenon of reversible π-dimerization in a stable neutral phenoxyl radical.
  • To characterize the structure and bonding of the observed π-dimer.
  • To explore the factors contributing to the stability of the π-dimer.

Main Methods:

  • Spectroscopic characterization (e.g., UV-Vis, EPR) of the phenoxyl radical and its dimer.
  • Experimental studies in solution under varying temperatures.
  • Density Functional Theory (DFT) and ab initio molecular orbital theory calculations.

Main Results:

  • Reversible π-dimerization of 2,6-bis-(8-quinolylamino)-4-(tert-butyl)phenoxyl (BAQP) was observed in solution.
  • The π-dimer exhibits strong bonding interactions between the phenoxyl rings.
  • Dispersion interactions between the quinolyl rings significantly contribute to dimer stability.

Conclusions:

  • The study demonstrates a novel instance of reversible π-dimerization in phenoxyl radicals.
  • The findings highlight the importance of multicenter bonding and non-covalent interactions in stabilizing radical dimers.
  • This research provides insights into the formation of extended bonding networks in radical systems.