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Issue 42, 2020
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Addition of carbon-centered radicals to aromatic antioxidants: mechanistic aspects

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Abstract

Several recent studies have shown that the rates of formation of adduct radicals between carbon-centred radicals and aromatic molecules are virtually diffusion-controlled and reversible. This contrasts with “radical addition”, the well-known multistep reaction in preparative organic chemistry where the rate-determining initial formation of radical adducts is perceived to be several orders of magnitude slower and virtually irreversible. Using pulse radiolysis and spectroscopic analysis, we have now re-examined parts of this complex mechanism. The results have significant implications for biological systems: electron-rich, aromatic structures may act like buffers for radicals, moderating their reactivity resulting in a much slower reaction determining the overall rate of oxidation. In vivo, an organism would gain time for an appropriate antioxidant reaction.

Graphical abstract: Addition of carbon-centered radicals to aromatic antioxidants: mechanistic aspects

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Article information


Submitted
24 Aug 2020
Accepted
16 Oct 2020
First published
19 Oct 2020

This article is Open Access

Phys. Chem. Chem. Phys., 2020,22, 24572-24582
Article type
Paper

Addition of carbon-centered radicals to aromatic antioxidants: mechanistic aspects

T. Nauser and J. M. Gebicki, Phys. Chem. Chem. Phys., 2020, 22, 24572
DOI: 10.1039/D0CP04469E

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