Synthesis, structure and basicity of 1,9-bis(dimethylamino)-dibenzothiophene and 1,9-bis(dimethylamino)-dibenzoselenophene1,2)

✍ Scribed by Heinz A. Staab; Matthias Höne; Claus Krieger

• Book ID: 104217517
• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 295 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)82074-2

✦ Synopsis

In the context of studies on bis(dialkylamino)arenes with neighbouring amino functions the title compounds 5 and 6 were synthesized. Their structures and those of the monoprotonated cations Sa and 6a were determined by X-ray analysis. The strong basicities of 5 and 6 (pKa = 11.9 and 11.8 f 0.1) are discussed in terms of lone pair interactions in 5 and 6 and the geometry of the WEN hydrogen bonds in 5a and 6a.