Dodeka(ethylene)octamine.

Because of their great potential in organic synthesis, design of proton sponges and superbases remains an active area of research. Nitrogen bases are very popular for this purpose, and the most common design principles involve destabilization of the base by enforcing close proximity of nitrogen lone pairs through rigid scaffolds and stabilization of the conjugate acid by intramolecular hydrogen bonds and extended, polarizable π-systems. The classic proton sponge, 1,8-bis(dimethylamino)naphthalene (1), 3 ] is the paradigmatic prototype that has spawned many variations.

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