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Issue 67, 2012

Is cyclobutadiene really highly destabilized by antiaromaticity?§

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Abstract

The high energy of cyclobutadiene (CBD) is not due primarily to “anti-aromaticity,” but rather to angle strain, torsional strain, and Pauli repulsion between the parallel CC bonds. Estimations including block-localized wavefunction (BLW) computations conclude that the enormous ring strain (ca. 60 kcal mol−1) far exceeds its antiaromatic destabilization (only 16.5 kcal mol−1).

Graphical abstract: Is cyclobutadiene really highly destabilized by antiaromaticity?

  • This article is part of the themed collection: Aromaticity

Supplementary files

Article information


Submitted
15 May 2012
Accepted
07 Jun 2012
First published
13 Jun 2012

Chem. Commun., 2012,48, 8437-8439
Article type
Communication

Is cyclobutadiene really highly destabilized by antiaromaticity?

J. I. Wu, Y. Mo, F. A. Evangelista and P. von Ragué Schleyer, Chem. Commun., 2012, 48, 8437 DOI: 10.1039/C2CC33521B

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