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The Bicorannulenyl Dianion: A Charged Overcrowded Ethylene
Author(s) -
Eisenberg David,
Jackson Edward A.,
Quimby Jennifer M.,
Scott Lawrence T.,
Shenhar Roy
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201002515
Subject(s) - diastereomer , character (mathematics) , ethylene , double bond , corannulene , chemistry , connection (principal bundle) , computational chemistry , crystallography , stereochemistry , polymer chemistry , organic chemistry , molecule , catalysis , mathematics , geometry
Super bowl : Bicorannulenyl, a large biaryl composed of two corannulene bowls, effectively becomes an overcrowded ethylene upon reduction to form a dianion (see picture). DFT calculations and NMR spectroscopic experiments reveal the double‐bond character of the connection between the two bowls. Three stable diastereomers that interconvert through bowl inversions and central bond rotations were shown to exist.