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“Proton sponge” analogues;Orientation dependence of hydrogen bonds;Crystal structures
Abstract:
1,2,4,5-Tetrakis(dimethylamino)benzene (4) and 2,3,6,7-tetrakis (dimethylamino)naphthalene (5) were prepared and structurally determined. Electron-donor functions, protonation, and the geometry of intramolecular hydrogen bonds are discussed. By oxidation of 4 to its dication the benzenoid aromaticity is cancelled in favour of two independent units as determined by X-ray structure aromaticity is cyanine-type analysis