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Symmetric Halogen Bonding is Preferred in Solution

Journal article
Authors Anna-Carin Carlsson
Jürgen Gräfenstein
Adnan Budnjo
Jonas Bergquist
Alavi Karim
Roland Kleinmaier
Ulrika Brath
Mate Erdelyi
Published in Journal of the American Chemical Society
Volume 134
Pages 5706-5715
ISSN 0002-7863
Publication year 2012
Published at Swedish NMR Centre at Göteborg University
Department of Chemistry and Molecular Biology
Pages 5706-5715
Language en
Subject categories Organic synthesis, Physical organic chemistry, Medicinal Chemistry, Pharmaceutical chemistry


Halogen bonding is a recently rediscovered secondary interaction that shows potential to become a complementary molecular tool to hydrogen bonding in rational drug design and in material sciences. Whereas hydrogen bond symmetry has been the subject of systematic studies for decades, the understanding of the analogous three-center halogen bonds is yet in its infancy. The isotopic perturbation of equilibrium (IPE) technique with 13C NMR detection was applied to regioselectively deuterated pyridine complexes to investigate the symmetry of [N−I−N]+ and [N−Br−N]+ halogen bonding in solution. Preference for a symmetric arrangement was observed for both a freely adjustable and for a conformationally restricted [N−X−N]+ model system, as also confirmed by computation on the DFT level. A closely attached counterion is shown to be compatible with the preferred symmetric arrangement. The experimental observations and computational predictions reveal a high energetic gain upon formation of symmetric, three-center four-electron halogen bonding. Whereas hydrogen bonds are generally asymmetric in solution and symmetric in the crystalline state, the analogous bromine and iodine centered halogen bonds prefer symmetric arrangement in solution.

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