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Synthesis and Characterization of 16π Antiaromatic 2,7-Dihydrodiazapyrenes: Antiaromatic Polycyclic Hydrocarbons with Embedded Nitrogen
- Source :
- Angewandte Chemie (International ed. in English). 60(25)
- Publication Year :
- 2021
-
Abstract
- We describe the two-electron reduction of N , N' -dimethyl-2,7-diazapyrenium dications ( MDAP 2+ ), which afforded the corresponding reduced form ( MDAP 0 ) as a highly electron-rich 16π antiaromatic system. A single-crystal X-ray diffraction analysis of MDAP 0 revealed a distorted quinoidal structure with high bond-length alternation. The 1 H NMR spectrum of MDAP 0 exhibited a diagnostic proton signal (4.6 ppm) that is distinctly upfield shifted compared to that of aromatic diazapyrene (8.3 ppm). Theoretical calculations supported the existence of a paratropic ring current. These results indicate that MDAP 0 exhibits antiaromatic character derived from its peripheral 16π-electron conjugation.
Details
- ISSN :
- 15213773
- Volume :
- 60
- Issue :
- 25
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie (International ed. in English)
- Accession number :
- edsair.doi.dedup.....0ab0e576a73d6f5cc013ac698711a593