1,8-Bis(dimethylamino)naphthalene

1,8-Bis(Dimethylamino)Naphthalene

1,8-Bis(dimethylamino)naphthalene

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Description:
1,8-Bis(dimethylamino)naphthalene is a chemical compound that was first prepared in 1968 by Roger Alder FRS at the University of Bristol. It is often referred by the trade name Proton Sponge, a trademark of Sigma-Aldrich. This compound is a diamine in which the two dimethylamino groups are attached on the same side or peri position of a naphthalene system. Proton-sponge has several very interesting properties; one is its very high basicity; another is its spectroscopic properties.

Structure and properties

With a pK<sub>a</sub> of 12.1 for its conjugate acid in aqueous solution, 1,8-bis(dimethylamino)naphthalene is one of the strongest amine bases known, although 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. However, the molecule 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.

The spectroscopic properties of Proton-sponge are very interesting for researchers of molecular chemistry and have been researched for a long time. Proton-sponge emits a double fluorescence in...
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