Competition between Halogen, Hydrogen and Dihydrogen Bonding in Brominated Carboranes

Jindřich Fanfrlík, Josef Holub, Zdeňka Růžičková, Jan Řezáč, Paul D Lane, Derek A. Wann, Drahomir Hnyk, Aleš Růžička, Pavel Hobza

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Abstract

Halogen bonds are a subset of noncovalent interactions with rapidly expanding applications in materials and medicinal chemistry. While halogen bonding is well known in organic compounds, it is new in the field of boron cluster chemistry. We have synthesized and crystallized carboranes containing Br atoms in two different positions, namely, bound to C- and B-vertices. The Br atoms bound to the C-vertices have been found to form halogen bonds in the crystal structures. In contrast, Br atoms bound to B-vertices formed hydrogen bonds. Quantum chemical calculations have revealed that halogen bonding in carboranes can be much stronger than in organic architectures. These findings open new possibilities for applications of carboranes, both in materials and medicinal chemistry.
Original languageEnglish
Pages (from-to)3373–3376
Number of pages4
JournalChemPhysChem
Volume17
Issue number21
Early online date22 Sep 2016
DOIs
Publication statusPublished - 4 Nov 2016

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    Fanfrlík, J., Holub, J., Růžičková, Z., Řezáč, J., Lane, P. D., Wann, D. A., Hnyk, D., Růžička, A., & Hobza, P. (2016). Competition between Halogen, Hydrogen and Dihydrogen Bonding in Brominated Carboranes. ChemPhysChem, 17(21), 3373–3376. https://doi.org/10.1002/cphc.201600848