Issue 67, 2012
From the journal:

Chemical Communications

Is cyclobutadiene really highly destabilized by antiaromaticity?†‡§

Judy I-Chia Wu,*a   Yirong Mo,b   Francesco Alfredo Evangelistac  and  Paul von Ragué Schleyer*a  

* Corresponding authors

a Department of Chemistry, Center for Computational Quantum Chemistry, University of Georgia, Athens, USA
E-mail: judywu@ccc.uga.edu, schleyer@chem.uga.edu
Fax: (+1) 706 542 0406

b Department of Chemistry, Western Michigan University, Kalamazoo, USA
E-mail: yirong.mo@wmich.edu

c Department of Chemistry, Yale University, New Haven, USA
E-mail: francesco.evangelista@yale.edu

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
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Article information

DOI
https://doi.org/10.1039/C2CC33521B
Article type
Communication
Submitted
15 ሜይ 2012
Accepted
07 ጁን 2012
First published
13 ጁን 2012

Chem. Commun., 2012,48, 8437-8439

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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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