1,8-Bis(dimethylamino)naphthalene

N, N, N ', N'- tetramethylnaphthalene -1, 8 -diamine (IUPAC)

45-49 ° C

12.34

Insoluble in water

Attention

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1,8-bis ( N, N- dimethylamino) naphthalene is an organic compound. It was first produced in 1968 by Roger Alder at the University of Bristol. It is referred to as a model substance of a proton sponge. 1,8-bis (dimethylamino ) naphthalene is an aromatic diamine having two tertiary amino groups in the adjacent position (peri - position) on the naphthalene ring. Through this position, a very high basicity (pKa = 12.34 ) and special spectroscopic properties result.

Structure and Properties

With a base constant of 12.34 is 1,8-bis (dimethylamino) naphthalene, one of the strongest amine bases known. Nevertheless, protons are taken up slowly. Because of its high basicity and low nucleophilicity, it is used in the organic synthesis as a means for deprotonating organic compounds.

Production

The compound is commercially available. They can be prepared by methylation of 1,8-diaminonaphthalene with methyl iodide or dimethyl sulfate.

Other proton sponges

Proton sponges of the second generation, with a still higher basicity, are 1,8-bis ( hexamethyltriaminophosphazenyl ) naphthalene or 1,8- bis ( hexamethyltriaminophosphazenyl ) naphthalene, HMPN: A superbasisches Bisphosphazen proton sponge is made from 1,8-bis (dimethylamino ) naphthalene and tris (dimethylamino ) phosphine prepared. HMPN has a pKBH 29.9 in acetonitrile.