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Syntheses, Structures and Basicities of 1,2,4,5‐Tetrakis(dimethylamino)benzene and 2,3,6,7‐Tetrakis(dimethylamino)naphthalene
Author(s) -
Staab Heinz A.,
ElblWeiser Karin,
Krieger Claus
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200001)2000:2<327::aid-ejoc327>3.0.co;2-z
Subject(s) - chemistry , dication , intramolecular force , naphthalene , protonation , benzene , aromaticity , hydrogen bond , cyanine , medicinal chemistry , photochemistry , stereochemistry , molecule , organic chemistry , ion , physics , quantum mechanics , fluorescence
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 cyanine‐type units as determined by X‐ray structure analysis.