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The Dominant Role of Chalcogen Bonding in the Crystal Packing of 2D/3D Aromatics
Author(s) -
Fanfrlík Jindřich,
Přáda Adam,
Padělková Zdeňka,
Pecina Adam,
Macháček Jan,
Lepšík Martin,
Holub Josef,
Růžička Aleš,
Hnyk Drahomír,
Hobza Pavel
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201405901
Subject(s) - chalcogen , heteroatom , sulfur , chemistry , boron , crystal engineering , crystallography , non covalent interactions , icosahedral symmetry , halogen bond , halogen , crystal structure , computational chemistry , organic chemistry , molecule , hydrogen bond , ring (chemistry) , supramolecular chemistry , alkyl
The chalcogen bond is a nonclassical σ‐hole‐based noncovalent interaction with emerging applications in medicinal chemistry and material science. It is found in organic compounds, including 2D aromatics, but has so far never been observed in 3D aromatic inorganic boron hydrides. Thiaboranes, harboring a sulfur heteroatom in the icosahedral cage, are candidates for the formation of chalcogen bonds. The phenyl‐substituted thiaborane, synthesized and crystalized in this study, forms sulfur⋅⋅⋅π type chalcogen bonds. Quantum chemical analysis revealed that these interactions are considerably stronger than both in their organic counterparts and in the known halogen bond. The reason is the existence of a highly positive σ‐hole on the positively charged sulfur atom. This discovery expands the possibilities of applying substituted boron clusters in crystal engineering and drug design.