text: This compound is a diamine in which the two dimethylamino groups are attached on the same side (peri position) of a naphthalene ring. This molecule has several very interesting properties; one is its very high basicity; another is its spectroscopic properties.
  With a pK of 12.34 for its conjugate acid in aqueous solution, 1,8-bis(dimethylamino)naphthalene is one of the strongest organic bases. However, it only absorbs protons slowly—hence the trade name. The high basicity is attributed to the relief of strain upon protonation and/or the strong interaction between the nitrogen lone pairs. Additionally, although many aromatic amines such as aniline show reduced basicity (due to nitrogen being sp hybridized; its lone pair occupying a 2p orbital and interacting and being withdrawn by the aromatic ring), this is not possible in this molecule, as the nitrogens' methyl groups prevent its substituents from adopting a planar geometry, as this would require forcing methyl groups from each nitrogen atom into one another—thus the basicity is not reduced by this factor which is found in other molecules. It is sterically hindered, making it a weak nucleophile. Because of this combination of properties, it has been used in organic synthesis as a highly selective non-nucleophilic base.
  Proton sponge also exhibits a very high affinity for boron and is capable of displacing hydride from borane to form a boronium–borohydride ion pair.