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Title
Japanese: 
English:Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes 
Author
Japanese: Y. Ishigaki, K. Asai, T. Shimajiri, 芥川 智行, 福島 孝典, T. Suzuki.  
English: Y. Ishigaki, K. Asai, T. Shimajiri, T. Akutagawa, T. Fukushima, T. Suzuki.  
Language English 
Journal/Book name
Japanese: 
English:Organic Materials 
Volume, Number, Page Vol. 3    Issue 2    Page 90-96
Published date Apr. 1, 2021 
Publisher
Japanese: 
English: 
Conference name
Japanese: 
English: 
Conference site
Japanese: 
English: 
Official URL https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0041-1725046
 
DOI https://doi.org/10.1055/s-0041-1725046
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.

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