Extended Hydrogen Bond Network Enabled Superbases

New superbases, those organic compounds whose basicities are greater than that of proton sponge, are suggested that involve extended hydrogen-bonding networks. Addition of aminoethyl and related groups to the 1,8-diaminonaphthalene framework provide second- and third-layer hydrogen bonding in the conjugate base. DFT computations predict these compounds to be 10–15 kcal mol–1 more basic than the proton sponge.