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 ButLi in tetrahydrofuran (thf) affords a laterally metallated derivative which exists as a tris(thf) solvated monomer with no Li–C interaction and an sp2 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.