Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes

Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes

Abstract The crystal structures of a series of tetracyanonaphthoquinodimethanes fused with a selenadiazole or thiadiazole ring revealed that their molecular packing is determined mainly by two intermolecular interactions: chalcogen bond (ChB) and weak hydrogen bond (WHB). ChB between Se and a cyano...

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Bibliographic Details
Main Authors: Yusuke Ishigaki, Kota Asai, Takuya Shimajiri, Tomoyuki Akutagawa, Takanori Fukushima, Takanori Suzuki
Format: Article
Language:English
Published: Georg Thieme Verlag 2021-04-01
Series:Organic Materials
Subjects:
crystal engineering
weak hydrogen bonds
chalcogen bonds
chalcogenadiazoles
tetracyanoquinodimethanes
x-ray analysis
Online Access:http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1725046
Description
Summary:Abstract The crystal structures of a series of tetracyanonaphthoquinodimethanes fused with a selenadiazole or thiadiazole ring revealed that their molecular packing is determined mainly by two intermolecular interactions: chalcogen bond (ChB) and weak hydrogen bond (WHB). ChB between Se and a cyano group dictates the packing of selenadiazole derivatives, whereas the S-based ChB is much weaker and competes with WHB in thiadiazole analogues. This difference can be explained by different electrostatic potentials as revealed by density functional theory calculations. A proper molecular design that weakens WHB can change the contribution of ChB in determining the crystal packing of thiadiazole derivatives.
ISSN:2625-1825

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