About the Antiaromaticity of Planar Cyclooctatetraene

Frank-Gerrit Klärner

doi:10.1002/1521-3773(20011105)40:21<3977::AID-ANIE3977>3.0.CO;2-N

About the Antiaromaticity of Planar Cyclooctatetraene

Angew Chem Int Ed Engl. 2001 Nov 5;40(21):3977-3981. doi: 10.1002/1521-3773(20011105)40:21<3977::AID-ANIE3977>3.0.CO;2-N.

Author

Frank-Gerrit Klärner¹

Affiliation

¹ Institut für Organische Chemie, Universität Essen 45117 Essen (Germany) Fax: (+49) 201-1834252.

PMID: 29712230
DOI: 10.1002/1521-3773(20011105)40:21<3977::AID-ANIE3977>3.0.CO;2-N

Abstract

A negligible antiaromatic destabilization is found in planar D_4h 1,3,5,7-cyclooctatetraene with alternating bond lengths. The same is also true for the delocalized D_8h structure, which has a stabilization energy of only 3-4 kcal mol^-1 . According to quantum-chemical calculations, the ground state of 1 is expected to be the planar C_2v -symmetric (1,1) singlet diradical 1'.

Keywords: antiaromaticity; cyclooctatetraene; diradicals; resonance energy.