On the stability of large [4n]annulenes

Chaitanya S. Wannere, Damian Moran, Norman L. Allinger, B. Andes Hess, Lawrence J. Schaad, Paul Von Ragué Schleyer*

*Corresponding author for this work

Research output: Contribution to journalArticle

87 Citations (Scopus)

Abstract

(Matrix presented) The stabilization energies (B3LYP/6-31G*) of planar [4n]annulenes, evaluated by a new indene-isoindene isomerization method (see Abstract graphic), reveal that all 4n π-electron rings larger than the energetically unfavorable cyclobutadiene are only slightly destabilized by the π-electron interactions. Cyclooctatetraene prefers the "tub" conformation because of strain effects. Generally, the antiaromatic character of the larger systems with 4n π-electrons is revealed best by their magnetic properties rather than by their energies.

Original languageEnglish
Pages (from-to)2983-2986
Number of pages4
JournalOrganic Letters
Volume5
Issue number17
DOIs
Publication statusPublished - 21 Aug 2003
Externally publishedYes

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