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Spherical Homoaromaticity
Author(s) -
Chen Zhongfang,
Jiao Haijun,
Hirsch Andreas,
von Ragué Schleyer Paul
Publication year - 2002
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 - 10.1002/1521-3773(20021115)41:22<4309::aid-anie4309>3.0.co;2-e
Subject(s) - computer science
The 2(N+1) 2 electron‐counting rule for spherical aromaticity can also be applied to spherical homoaromatic systems: The adamantane‐, cubane‐, and dodecahedrane‐based species containing two or eight delocalized electrons were designed by bridging the sp 2 carbon atoms of highly symmetrical ( T d , T h ) carbon polyhedrane units. Their aromatic character was demonstrated by the highly negative nucleus‐independent chemical shift (NICS) values at the cage centers, for example C 20 H 12 (see picture) has an NICS value of −36.4 ppm.