Isomeric Tetrakis(dimethylamino)naphthalenes: Syntheses, Structure-Dependence of Basicities, Crystal Structures, and Physical Properties

✍ Scribed by Heinz A. Staab; Annette Kirsch; Thomas Barth; Claus Krieger; Franz A. Neugebauer

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 326 KB
• Volume: 2000
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(200004)2000:8<1617::aid-ejoc1617>3.0.co;2-c

✦ Synopsis

Tetrakis(dimethylamino)naphthalenes / Basicity / Hydrogen bonds / Cyclovoltammetry For comparison to the recently described 2,3,6,7-tetrakis(dimethylamino)naphthalene (1) the three isomers 2, 3, and 4 were synthesized. The basicities of this group of isomers are strongly dependent upon the different mutual orientations of the pairs of dimethylamino substituents: only the isomers 3 and, partially, 4, both with dimethylamino groups in adjacent peri-positions of the naphthalene, are strong ''proton sponges''. For the isomers 1 and 2 with the same number and kind of twofold dimethylamino substituents in neighbouring ortho-positions, however, no significant basicity increase is observed. To explain this difference between the two groups [ ] Part 13: Ref.