Format

Send to

Choose Destination
See comment in PubMed Commons below
Nat Commun. 2013;4:1448. doi: 10.1038/ncomms2473.

A six-carbon 10π-electron aromatic system supported by group 3 metals.

Author information

1
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA.

Abstract

Aromaticity is a fundamental concept with implications spanning all the chemical sciences. Hückel's (4n+2)π-electron rule is the standard criterion to determine aromaticity and it applies well to neutral arenes as well as to charged species such as the cyclopentadienyl anion, the cyclooctatetraene dianion and the cycloheptatrienyl cation (tropylium). In the series of all-carbon aromatic compounds, no example of a benzene tetraanion, which is theoretically a 6C, 10π-electron aromatic system, has been reported although heteroatom analogues of such a system, known as 'electron-rich aromatics', have been studied in detail for a long time. Here we present the isolation of the first tetraanionic-substituted benzene as a ligand coordinated to group 3 metals. The nature of the substituted benzene tetraanion and the aromaticity of the 6C, 10π-electron system were established by X-ray crystallographic studies, multi-nuclei nuclear magnetic resonance spectroscopy, X-ray absorption spectroscopy and density functional theory calculations.

PMID:
23385592
DOI:
10.1038/ncomms2473
[Indexed for MEDLINE]
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for Nature Publishing Group
    Loading ...
    Support Center