Aromaticity and curvature in heteroacepentalenes

Mark Mascal

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

(Chemical Equation Presented) Heteroatom-substituted acepentalene derivatives which are isoelectronic with the known acepentalenediide dianion are nonplanar, fused aromatic tricycles which are hemifullerenes of the corresponding C20 heteroanalogue. Depending on the number and position of heteroatoms, they may be anionic, neutral, or cationic. A nucleus-independent chemical shift study indicates that substitution of the central carbon of the acepentalenediide system with N or O results in a substantial increase in aromaticity. Peripheral aza substitution on the other hand tends to increase curvature and decrease aromaticity. Alkylation or protonation at the central position of asymmetrically substituted heteroacepentalenides leads to chiral, bowl-shaped, 10π aromatic species.

Original languageEnglish (US)
Pages (from-to)4323-4327
Number of pages5
JournalJournal of Organic Chemistry
Volume72
Issue number12
DOIs
Publication statusPublished - Jun 8 2007

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry

Cite this