Issue 37, 2011
From the journal:

Physical Chemistry Chemical Physics

Aromaticity of strongly bent benzene rings: persistence of a diatropic ring current and its shielding cone in [5]paracyclophane†

Leonardus W. Jenneskens,*a   Remco W. A. Havenith,b   Alessandro Soncinic  and  Patrick W. Fowler*d  

* Corresponding authors

a Organic Chemistry & Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG Utrecht, Netherlands
E-mail: l.w.jenneskens@uu.nl
Fax: +31-30-2523615
Tel: +31-30-2533128

b Theoretical Chemistry, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG Groningen, Netherlands
E-mail: r.w.a.havenith@rug.nl

c School of Chemistry, University of Melbourne, Victoria 3010, Australia
E-mail: asoncini@unimelb.edu.au

d Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK
E-mail: P.W.Fowler@sheffield.ac.uk

Abstract

Direct evaluation of the induced π current density in [5]paracyclophane (1) shows that, despite the significant non-planarity (α = 23.2°) enforced by the pentamethylene bridge, there is only a modest (ca. 17%) reduction in the π ring current, justifying the use of shielding-cone arguments for the assignment of 1H NMR chemical shifts of 1 and the claim that the non-planar benzene ring in 1 retains its aromaticity (on the magnetic criterion).

Graphical abstract: Aromaticity of strongly bent benzene rings: persistence of a diatropic ring current and its shielding cone in [5]paracyclophane

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Article information

DOI
https://doi.org/10.1039/C1CP21950B
Article type
Paper
Submitted
15 Jun 2011
Accepted
03 Aug 2011
First published
23 Aug 2011

Phys. Chem. Chem. Phys., 2011,13, 16861-16866

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Aromaticity of strongly bent benzene rings: persistence of a diatropic ring current and its shielding cone in [5]paracyclophane

L. W. Jenneskens, R. W. A. Havenith, A. Soncini and P. W. Fowler, Phys. Chem. Chem. Phys., 2011, 13, 16861 DOI: 10.1039/C1CP21950B

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