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Competition between Halogen, Hydrogen and Dihydrogen Bonding in Brominated Carboranes
Author(s) -
Fanfrlík Jindřich,
Holub Josef,
Růžičková Zdeňka,
Řezáč Jan,
Lane Paul D.,
Wann Derek A.,
Hnyk Drahomír,
Růžička Aleš,
Hobza Pavel
Publication year - 2016
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201600848
Subject(s) - halogen , halogen bond , chemistry , hydrogen bond , non covalent interactions , cluster (spacecraft) , boron , crystal engineering , cluster chemistry , crystallography , molecule , organic chemistry , alkyl , computer science , programming language
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.