Aminoxyl group

Aminoxyl radicals are chemical species containing the R₂N–O• functional group. They are also known as nitroxyl radicals and nitroxides, however IUPAC discourages the use of these terms, as they erroneously suggest the presence of a nitro group.^[1] They are radicals and are structurally related to oximes (hydroxylamines) and N-oxoammonium salts, with which they can interconvert via a series of redox steps.

Sterically hindered aminoxyls such TEMPO and TEMPOL are persistent (stable) radicals and find use in a range of oxoammonium-catalyzed oxidations. They are also present as transitory species various polymer stabilizers such as hindered amine light stabilizers and some p-phenylenediamine based antiozonants.^[2]

References

^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "aminoxyl radicals". doi:10.1351/goldbook.A00285
^ Cataldo, Franco (January 2018). "Early stages of p-phenylenediamine antiozonants reaction with ozone: Radical cation and nitroxyl radical formation". Polymer Degradation and Stability. 147: 132–141. doi:10.1016/j.polymdegradstab.2017.11.020.

[1] IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "aminoxyl radicals". doi:10.1351/goldbook.A00285

[2] Cataldo, Franco (January 2018). "Early stages of p-phenylenediamine antiozonants reaction with ozone: Radical cation and nitroxyl radical formation". Polymer Degradation and Stability. 147: 132–141. doi:10.1016/j.polymdegradstab.2017.11.020.

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See Also

References