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Spin-Spin Coupling Between Two meta-Benzyne Moieties In a Quinolinium Tetraradical Cation Increases Their Reactivities. | LitMetric
The reactivity of a carbon-centered σ,σ,σ,σ-type singlet-ground-state tetraradical containing two meta-benzyne moieties was examined in the gas phase. Surprisingly, the tetraradical showed higher reactivity than its individual meta-benzyne counterparts. The reactivity of meta-benzynes is controlled by their (calculated) distortion energy ΔE , singlet-triplet spitting ΔE , and electron affinity (EA ) of the meta-benzyne moiety at the transition state geometry for hydrogen-atom abstraction reactions. The addition of a second meta-benzyne moiety to a meta-benzyne does not significantly change EA . However, ΔE is substantially decreased for both meta-benzyne moieties in the tetraradical, and this explains their higher reactivities. The decrease in ΔE for each meta-benzyne moiety in the tetraradical is rationalized by stabilizing spin-spin coupling between one radical site in each meta-benzyne moiety. Therefore, spin-spin coupling between the meta-benzyne moieties in this tetraradical increases its reactivity, whereas spin-spin coupling within each meta-benzyne moiety decreases its reactivity.
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