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Issue 11, 2014

A solvent-resistant halogen bond

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Abstract

The effect of solvent on the stabilities of complexes involving a single H-bond or halogen-bond (X-bond) has been quantified. Association constants for binary complexes of 4-(phenylazo)phenol, molecular iodine, tetramethylurea and tetramethylthiourea have been measured in fifteen different solvents by UV/vis absorption and 1H NMR titration experiments. The stabilities of the H-bonded complexes decrease by more than three orders of magnitude with increasing solvent polarity. In contrast, the X-bonded complex of molecular iodine with tetramethylthiourea is remarkably insensitive to the nature of the solvent (association constants measured in alkanes and alcohols are similar). The results suggest that, in contrast to H-bonds, where electrostatics determine thermodynamic stability, charge-transfer interactions make a major contribution to the stability of these X-bonded complexes rendering them resistant to increases in solvent polarity.

Graphical abstract: A solvent-resistant halogen bond

Supplementary files

Article information


Submitted
12 Jun 2014
Accepted
09 Jul 2014
First published
30 Jul 2014

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2014,5, 4179-4183
Article type
Edge Article
Author version available

A solvent-resistant halogen bond

C. C. Robertson, R. N. Perutz, L. Brammer and C. A. Hunter, Chem. Sci., 2014, 5, 4179 DOI: 10.1039/C4SC01746C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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