How can breaking a nitrogen-nitrogen bond form a free radical?

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In chemistry, a free radical is a molecule containing at least one unpaired electron. Most radicals are formed through the cleavage of normal electron-pair covalent bonds, where the bond breaks to produce two separate entities, each retaining one electron from the original shared pair.1

The formation of free radicals via the breaking of a nitrogen-nitrogen (N–N) bond occurs in specific chemical structures, such as aromatic hydrazines (general structure R2N–NR2) or the central N–N bond in aromatic tetrazanes (R2N–RN–NR–NR2). When these bonds undergo cleavage, the shared electron pair is split, resulting in the formation of two radicals, each with an unpaired electron on a nitrogen atom.21

While many simple radicals are highly reactive and short-lived, certain radicals formed from N–N bond cleavage can be stabilized through structural features like resonance, which allows for the delocalization of the unpaired electron and increases the molecule's stability.12