Counterion influence on the N–I–N halogen bond
Bedin, M., Karim, A., Reitti, M., Carlsson, A.-C. C., Topic, F., Cetina, M., Pan, F., Havel, V., Al-Ameri, F., Sindelar, V., Rissanen, K., Gräfenstein, J., & Erdély, M. (2015). Counterion influence on the N–I–N halogen bond. Chemical Science, 6(7), 3746-3756. https://doi.org/10.1039/C5SC01053E
Julkaistu sarjassa
Chemical ScienceTekijät
Päivämäärä
2015Tekijänoikeudet
© 2015 The Authors. Published by The Royal Society of Chemistry. This is an Open Access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work in properly cited. The Creative Commons Public Domain Dedication waiver applies to the data made available in this article, unless otherwise stated.
A detailed investigation of the influence of counterions on the [N–I–N]+ halogen bond in solution, in the
solid state and in silico is presented. Translational diffusion coefficients indicate close attachment of
counterions to the cationic, three-center halogen bond in dichloromethane solution. Isotopic
perturbation of equilibrium NMR studies performed on isotopologue mixtures of regioselectively
deuterated and nondeuterated analogues of the model system showed that the counterion is incapable
of altering the symmetry of the [N–I–N]+ halogen bond. This symmetry remains even in the presence of
an unfavorable geometric restraint. A high preference for the symmetric geometry was found also in the
solid state by single crystal X-ray crystallography. Molecular systems encompassing weakly coordinating
counterions behave similarly to the corresponding silver(I) centered coordination complexes. In contrast,
systems possessing moderately or strongly coordinating anions show a distinctly different behavior. Such
silver(I) complexes are converted into multi-coordinate geometries with strong Ag–O bonds, whereas
the iodine centered systems remain linear and lack direct charge transfer interaction with the
counterion, as verified by 15N NMR and DFT computation. This suggests that the [N–I–N]+ halogen bond
may not be satisfactorily described in terms of a pure coordination bond typical of transition metal
complexes, but as a secondary bond with a substantial charge-transfer character.
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Ellei muuten mainita, aineiston lisenssi on © 2015 The Authors. Published by The Royal Society of Chemistry. This is an Open Access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work in properly cited. The Creative Commons Public Domain Dedication waiver applies to the data made available in this article, unless otherwise stated.
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