Variations in the solid-state, solution and theoretical structures of a laterally deprotonated aromatic tertiary amide

Reaction of 2-ethyl-N,N-diisopropyl-1-naphthamide 3 with (BuLi)-Li-t in tetrahydrofuran (thf) affords a laterally metallated derivative which exists as a tris( thf) solvated monomer with no Li-C interaction and an sp(2) hybridised carbanionic centre in the solid-state; NMR spectroscopy suggests that this structure is viable in solution but that Li-C bonded atropisomers are also possible and calculations corroborate these data.