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Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

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This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.9K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Radical Chain-Growth Polymerization: Overview01:10

Radical Chain-Growth Polymerization: Overview

2.5K
Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
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Radical Chain-Growth Polymerization: Chain Branching01:17

Radical Chain-Growth Polymerization: Chain Branching

2.0K
The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
2.0K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Related Experiment Video

Updated: Aug 15, 2025

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

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Diradical B/N-Doped Polycyclic Hydrocarbons.

Jiaxiang Guo1, Zeyi Li1, Xinyu Tian1

  • 1State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, 130012, P. R. China.

Angewandte Chemie (International Ed. in English)
|January 4, 2023
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel B/N-type organic diradicaloids by extending a B/N-heterocycle with a quinoidal structure. These materials exhibit enhanced diradical character and magnetic properties, opening new avenues for organic electronics and spintronics.

Keywords:
AntiaromaticityDiradical CharacterDiradicaloidsPolycyclic HydrocarbonsQuinoidal Conjugation

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Last Updated: Aug 15, 2025

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A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Quantum Chemistry

Background:

  • Heterocyclic diradicaloids are crucial for advanced organic electronics and spintronics.
  • Precise control over open-shell electronic nature is key for material design.
  • Boron/Nitrogen (B/N)-doped systems offer unique electronic and magnetic properties.

Purpose of the Study:

  • To synthesize and characterize novel B/N-type organic diradicaloids.
  • To explore the impact of quinoidal π-extension on B/N-heterocycles.
  • To investigate the resulting electronic, magnetic, and photophysical properties.

Main Methods:

  • Synthesis of quinoidal π-extended B/N-doped polycyclic hydrocarbons.
  • Incorporation of B/N-heterocycle motifs with antiaromatic cores (s-indacene, dicyclopenta[b,g]naphthalene).
  • Spectroscopic and computational analyses to determine electronic structure and diradical character.

Main Results:

  • Successful synthesis of two novel B/N-type organic diradicaloids.
  • Demonstrated open-shell electronic nature due to quinoidal π-extension and B/N-heterocycle.
  • Enhanced diradical character and modulated (anti)aromaticity compared to all-carbon analogs.
  • Observed magnetic activities, narrow energy gaps, and highly red-shifted absorptions.

Conclusions:

  • Quinoidal π-extension of B/N-heterocycles effectively generates B/N-type organic diradicaloids.
  • These novel materials exhibit distinct electronic and magnetic properties.
  • This work expands the scope of B/N-doped polycyclic π-systems and heterocyclic diradicaloids for future applications.