stylistic:tone, linguistic:paraphrasing
Stability of organic radicals

The generation and reactivity of organic radicals are dependent on both their thermodynamic stability and the kinetic stability, also known as the persistency. This distinction is necessary because these two types of stability do not always correlate with each other. For example, benzylic radicals, which is known for its weak benzylic C−H bond strength, are thermodynamically stabilized due to resonance delocalization. However, these radicals kinetically transient because they can undergo rapid, diffusion-limited dimerization, resulting in a lifetime that is less than a few nanosecond. To avoid confusion, particularly for carbon-centered radicals, Griller and Ingold introduced the following definitions: "Stabilized should be used to describe a carbon-centered radical, R ·, when the R−H bond strength is weaker than the appropriate C−H bond of alkane." "Persistent should be used to describe a radical that has a lifetime that is significantly greater than methyl under the same condition." While relationships between thermodynamic stability and kinetic persistency is highly case dependent, organic radicals can be generally stabilized by any or all of these factors: presence of electronegativity, delocalization, and steric hindrance. The compound 2,2,6,6-tetramethylpiperidinyloxyl illustrates the combination of all three factors. It is a commercially available solid that, aside from being magnetic, behaves like a normal organic compound.