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
About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

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

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements