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Related Experiment Video

Updated: Sep 19, 2025

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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Radical Formation by Direct Single Electron Transfer between Nitrobenzene and Anionic Organo Bases.

Shivaprasad Achary Balahoju1, Nicholus Bhattacharjee1, Luis Lezama2

  • 1Donostia International Physics Centre (DIPC), Paseo Manuel Lardizabal 4, Donostia 20018, Euskadi, Spain.

ACS Omega
|June 16, 2025
PubMed
Summary

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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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.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
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Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions...
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A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Radical Formation: Abstraction00:47

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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.
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Researchers developed a new method to easily create organic radicals, which have unique properties. This approach uses nitrobenzene and common organic bases, enabling new applications for radical chemistry under mild conditions.

Area of Science:

  • Organic Chemistry
  • Physical Chemistry
  • Spectroscopy

Background:

  • Organic radicals possess unique magnetic and reactivity properties.
  • Their application is limited by the challenging chemistry and strict structural requirements for their preparation.
  • Facile radical formation under mild conditions is key to unlocking their potential.

Purpose of the Study:

  • To develop a general protocol for facile radical formation using readily available starting materials.
  • To explore nitroarenes as versatile radical precursors.
  • To investigate the potential of organic bases and nitrobenzene in radical generation.

Main Methods:

  • Electron paramagnetic resonance (EPR) spectroscopy.
  • Ab initio quantum chemical calculations.

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Last Updated: Sep 19, 2025

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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  • Single electron transfer reactions involving anionic organic bases and nitrobenzene.

    • Main Results:

    • An unprecedented single electron transfer from anionic organic bases (B-X+) to nitrobenzene was observed.
    • Stable nitrobenzenide radical ion-pairs [1•-]-[X+] and transient oxidized radical bases (B•) were formed.
    • Nitroarenes were established as effective radical precursors.

    Conclusions:

    • A broadly applicable protocol for generating heteroatom-centered radicals under mild conditions was established.
    • The study provides a method using inexpensive and readily available starting materials.
    • The [1]-[B-X+] couple presents a novel platform for frustrated radical pair research.