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New proton sponges, 13. - syntheses, structures and basicities of 1,2,4,5-tetrakis(dimethylamino)benzene and 2,3,6,7-tetrakis(dimethylamino)naphthalene

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Staab,  Heinz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Krieger,  Claus
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Staab, H. A., Elbl-Weiser, K., & Krieger, C. (2000). New proton sponges, 13. - syntheses, structures and basicities of 1,2,4,5-tetrakis(dimethylamino)benzene and 2,3,6,7-tetrakis(dimethylamino)naphthalene. European Journal of Organic Chemistry, 2000(2), 327-333. doi:10.1002/(SICI)1099-0690(200001)2000:2%3C327:AID-EJOC327%3E3.0.CO;2-Z.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0028-3719-0
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