A Lithium Amide Protected Against Protonation in the Gas Phase: Unexpected Effect of LiCl

In cold THF and in the presence of LiCl, a lithium pyrrolidinylamide forms a 1:1 mixed aggregate, which is observed directly by ESI-MS. Gas-phase protonation of this species leads to selective transfer of H⁺ to the chlorine, suggesting that LiCl shields the amide nitrogen and prevents its direct protonation