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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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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.
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Radical Substitution: Allylic Bromination01:27

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Radical Formation: Addition00:47

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Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
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The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
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The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
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Updated: Apr 20, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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A mixed arsenic-phosphorus centered biradicaloid.

Alexander Hinz1, Axel Schulz, Alexander Villinger

  • 1Institut für Chemie, Universität Rostock, Albert-Einstein-Strasse 3a, 18059 Rostock (Germany) http://www.schulz.chemie.uni-rostock.de/

Angewandte Chemie (International Ed. in English)
|November 19, 2014
PubMed
Summary

Researchers synthesized the first mixed phosphorus-arsenic cyclic compound with distinct radical centers. This novel arsaphosphadiazanediyl opens new avenues for exploring unique main-group biradicaloids.

Keywords:
arsenicbiradicalheterocyclephosphorussynthesis

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Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of ChalcogenidoplumbatesII or IV
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Area of Science:

  • Main-group inorganic chemistry
  • Organometallic chemistry
  • Radical chemistry

Background:

  • Main-group singlet biradicaloids, particularly cyclobutane-1,3-diyl derivatives, have been extensively studied.
  • Existing examples feature identical radical centers, limiting structural diversity.
  • A need exists for biradicaloids with distinct radical centers for novel electronic and chemical properties.

Purpose of the Study:

  • To synthesize a mixed dipnictadiazanediyl featuring phosphorus (P) and arsenic (As) with distinct radical characters.
  • To explore the chemistry of novel cyclic compounds containing both P and As.

Main Methods:

  • Synthesis of the unprecedented cyclodichloro arsaphosphadiazane [ClP(μ-NTer)2AsCl].
  • Treatment with a halide-abstracting agent to form a cyclic cation.
  • Reduction with magnesium to yield the target dipnictadiazanediyl.

Main Results:

  • Successful preparation of the novel cyclic cation [P(μ-NTer)2AsCl](+).
  • Isolation of the first arsaphosphadiazanediyl [P(μ-NTer)2As], featuring distinct P and As radical centers.
  • Demonstration of a synthetic route to mixed-element main-group biradicaloids.

Conclusions:

  • The study reports the first synthesis of a main-group biradicaloid with distinct phosphorus and arsenic radical centers.
  • The developed synthetic methodology provides access to a new class of mixed-element cyclic compounds.
  • This work expands the scope of known biradicaloid structures and their potential applications.