First, we find that the dimerization of the oxidised bases is calculated to always be exothermic ((2.1) in Figure , Scheme S12-S18, Table ), resulting in an overall reaction energy ∆𝐺 of -22, +4, 0, +1, -28, -26, and -24, kcal/mol for Na iPr Cp, LiO t Bu, NaO t Bu, KO t Bu, LiHMDS, NaHMDS, and KHMDS, respectively Radical dimerization of O t Bu• and HMDS• would yield di-tert-butyl peroxide and tetrakis(trimethylsilyl)hydrazine, which are relatively stable known compounds. However, comparative quantitative 1 H NMR DOSY experiments in d-THF of NaO t Bu and KHMDS, before and after reaction with [1] do not reveal large enough differences in the diffusion coefficients to account for dimerization (Figure & S49). Additionally, these differences could be ascribed to the formation of aggregates of NaO t Bu and KHMDS in THF, which would be disrupted by the formation of [1 •-]([X + ]). Thus, while this remains a predicted possible pathway, especially for the XHMDS bases, we have been unable to experimentally validate it.