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. 2012 Aug 28;48(67):8437-9.
doi: 10.1039/c2cc33521b. Epub 2012 Jul 16.

Is cyclobutadiene really highly destabilized by antiaromaticity?

Judy I-Chia Wu  1 , Yirong Mo, Francesco Alfredo Evangelista, Paul von Ragué Schleyer
Affiliations

Is cyclobutadiene really highly destabilized by antiaromaticity?

Judy I-Chia Wu et al. Chem Commun (Camb). .

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)).

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