The Radical Ions of Naphtho [1,8-cd]-[1,2,6]thiadiazine and Some of Its Derivatives

✍ Scribed by Fabian Gerson; Georges Plattner; Richard Bartetzko; Rolf Gleiter

• Publisher: John Wiley and Sons
• Year: 1980
• Tongue: German
• Weight: 428 KB
• Volume: 63
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19800630803

✦ Synopsis

Abstract

The radical cations and anions of naphtho [1,8‐cd]‐[1,2,6]thiadiazine (1) and 6,7‐dihydroacenaphtho [5, 6‐cd]‐[1,2,6]thiadiazine (2), as well as the radical anion of acenaphtho [5, 6‐cd]‐[1,2,6]thiadiazine (3) have been characterized by ESR. spectroscopy. The π‐spin distributions in the radical cations \documentclass{article}\pagestyle{empty}\begin{document}$ 1^{\oplus \atop \dot{}}$\end{document} and \documentclass{article}\pagestyle{empty}\begin{document}$ 2^{\oplus \atop \dot{}}$\end{document} strongly resemble those in the iso‐π‐electronic phenalenyl radical. A prominent feature of the radical anions \documentclass{article}\pagestyle{empty}\begin{document}$ 1^{\ominus \atop \dot{}}$\end{document}, \documentclass{article}\pagestyle{empty}\begin{document}$ 2^{\ominus \atop \dot{}}$\end{document} and \documentclass{article}\pagestyle{empty}\begin{document}$ 3^{\ominus \atop \dot{}}$\end{document} is the substantial localization of the π‐spin population on the thiadiazine fragment. These findings are satisfactorily accounted for by HMO models using conventional heteroatom parameters.