Aminoxyl denotes a radical functional group with general structure R2N–O•. It is commonly known as a nitroxyl radical or a nitroxide, however IUPAC discourages the use of these terms, as they erroneously suggest the presence of a nitro group. Aminoxyls are structurally related to hydroxylamines and N-oxoammonium salts, with which they can interconvert via a series of redox steps.
* The general structure of the aminoxyl radical
* TEMPO, a commonly encountered organic aminoxyl radical
* Fremy's salt, an inorganic aminoxyl radical
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| - Aminoxyl (cs)
- Aminoxyl group (en)
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| - Aminoxyl je název radikálových funkčních skupin s obecným vzorcem R2N–O•; často se označují jako nitroxylové radikály nebo nitroxidy, které ovšem Mezinárodní unie pro čistou a užitou chemii nedoporučuje, protože neobsahují nitroskupinu. Aminoxyly jsou strukturně podobné hydroxylaminům a N-oxoamonným solím, na které je lze přeměnit redoxními reakcemi. Stericky nezatížené aminoxyly s α-vodíky jsou nestálé a rychle se disproporcionují na nitrony a hydroxylaminy. Používají se i na tvorbu polymerů , ale i jako . Na aminoxylové radikály lze změnit i . (cs)
- Aminoxyl denotes a radical functional group with general structure R2N–O•. It is commonly known as a nitroxyl radical or a nitroxide, however IUPAC discourages the use of these terms, as they erroneously suggest the presence of a nitro group. Aminoxyls are structurally related to hydroxylamines and N-oxoammonium salts, with which they can interconvert via a series of redox steps.
* The general structure of the aminoxyl radical
* TEMPO, a commonly encountered organic aminoxyl radical
* Fremy's salt, an inorganic aminoxyl radical (en)
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| - Aminoxyl je název radikálových funkčních skupin s obecným vzorcem R2N–O•; často se označují jako nitroxylové radikály nebo nitroxidy, které ovšem Mezinárodní unie pro čistou a užitou chemii nedoporučuje, protože neobsahují nitroskupinu. Aminoxyly jsou strukturně podobné hydroxylaminům a N-oxoamonným solím, na které je lze přeměnit redoxními reakcemi. Stericky nezatížené aminoxyly s α-vodíky jsou nestálé a rychle se disproporcionují na nitrony a hydroxylaminy. Stericky zatížené aminoxyly bez α-vodíků, jako jsou TEMPO a TEMPOL, jsou stálými radikály a mají řadu využití v laboratořích i průmyslu. Mohou se vratně vázat na řadu sloučenin a také selektivně oxidovat karbonylové sloučeniny skrz . Slouží také jako a jako reaktivní složky p-fenylendiaminových antiozonantů. Používají se i na tvorbu polymerů , ale i jako . Na aminoxylové radikály lze změnit i . (cs)
- Aminoxyl denotes a radical functional group with general structure R2N–O•. It is commonly known as a nitroxyl radical or a nitroxide, however IUPAC discourages the use of these terms, as they erroneously suggest the presence of a nitro group. Aminoxyls are structurally related to hydroxylamines and N-oxoammonium salts, with which they can interconvert via a series of redox steps.
* The general structure of the aminoxyl radical
* TEMPO, a commonly encountered organic aminoxyl radical
* Fremy's salt, an inorganic aminoxyl radical Sterically unhindered aminoxyls baring α-hydrogens are unstable and undergo rapid disproportionation to nitrones and hydroxylamines. Sterically hindered aminoxyls without α-hydrogens, such TEMPO and TEMPOL, and are persistent (stable) radicals and find use in a range of applications, both on the laboratory scale and in industry. Their ability to reversibly bind to other radical compounds makes them important as both spin labels and spin traps. They are used to selectively oxidise carbonyl groups via oxoammonium-catalyzed oxidations. They are also used as polymer stabilizers such as hindered amine light stabilizers or as transient reactive species in p-phenylenediamine based antiozonants. They are used both to form polymers via nitroxide-mediated radical polymerization and prevent their formation as polymerization inhibitors. Various other reagents, such as N-hydroxyphthalimide can also be converted into aminoxyl radicals as part of their chemistry. (en)
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