The effects of intramolecular hydrogen bonding on the reactivity of phenoxyl radicals in model systems

- Gas-phase reactivity of phenoxyl radical cations of aromatic nitrogen bases is studied.
- Reactivity towards NO and C3H7SH decreases as N+-H⋯O distance decreases.
- Reactivity decreases as spin density at the oxygen atom decreases.
- LysTyr(O) radical cation is stabilized by hydrogen bonding at the radical site.