Aromatization of fulvene by complexation with lithium.
At the B3LYP/6-311++G(d,p) level, approach of a lithium atom to a face of the fulvene molecule leads to formation of a complex with binding energy 41 kcal/mol and significant ion-pair character. The fulvene moiety gains a delocalized aromatic cyclic π system, documented by the geometry-based aromaticity index HOMA, and a strong diatropic ring current, visualized by ipsocentric calculation of the π current-density, which leads to an "aromatic" NICS value of -11 ppm.
Oziminski
W P
WP
National Medicines Institute, Warsaw, Poland. wojozim@gmail.com
Krygowski
T M
TM
Fowler
P W
PW
Soncini
A
A
D003517:Cyclopentanes / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation
D003517:Cyclopentanes; C017332:fulvene; D008094:Lithium