Competition between Halogen, Hydrogen and Dihydrogen Bonding in Brominated Carboranes

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


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
Issue number21
Early online date5 Sept 2016
Publication statusPublished - 4 Nov 2016

Bibliographical note

© 2016 John Wiley & Sons, Inc. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.


  • bromine
  • carboranes
  • halogen bonds
  • sigma holes
  • X-ray crystal structure

Cite this