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Issue 27, 2013
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Intramolecular halogen–halogen bonds?

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Abstract

By analysing the properties of the electron density in the structurally simple perhalogenated ethanes, X3C–CY3 (X, Y = F, Cl), a previously overlooked non-covalent attraction between halogens attached to opposite carbon atoms is found. Quantum chemical calculations extrapolated towards the full solution of the Schrödinger equation reveal the complex nature of the interaction. When at least one of the halogens is a chlorine, the strength of the interaction is comparable to that of hydrogen bonds. Further analysis shows that the bond character is quite different from standard non-covalent halogen bonds and hydrogen bonds; no bond critical points are found between the halogens, and the σ-holes of the halogens are not utilised for bonding. Thus, the nature of the intramolecular halogen⋯halogen bonding studied here appears to be of an unusually strong van der Waals type.

Graphical abstract: Intramolecular halogen–halogen bonds?

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Article information


Submitted
04 Mar 2013
Accepted
08 May 2013
First published
08 May 2013

This article is Open Access

Phys. Chem. Chem. Phys., 2013,15, 11543-11553
Article type
Paper

Intramolecular halogenhalogen bonds?

M. P. Johansson and M. Swart, Phys. Chem. Chem. Phys., 2013, 15, 11543
DOI: 10.1039/C3CP50962A

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