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 aromati...

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Bibliographic Details
Published in:Organic letters 2010-11, Vol.12 (21), p.4880-4883
Main Authors: Oziminski, W. P, Krygowski, T. M, Fowler, P. W, Soncini, A
Format: Article
Language:English
Subjects:
Cyclopentanes - chemistry
Lithium - chemistry
Models, Molecular
Molecular Conformation
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol102037e