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- Title
Molecular Recognition by Chalcogen Bond: Selective Charge‐Transfer Crystal Formation of Dimethylnaphthalene with Selenadiazolotetracyanonaphthoquinodimethane.
- Authors
Ishigaki, Yusuke; Asai, Kota; Rouville, Henri‐Pierre Jacquot; Shimajiri, Takuya; Heitz, Valérie; Fujii‐Shinomiya, Hiroshi; Suzuki, Takanori
- Abstract
The title nonplanar electron acceptor (1) fused with a selenadiazole ring selectively forms a crystalline charge‐transfer complex (CT crystal) with 2,6‐dimethylnaphthalene (2,6‐DMN). On the other hand, the sulfur analogue (2) has less recognition ability and forms CT crystals with both 2,6‐ and 2,7‐DMN. X‐ray analyses of 1, 2, and their CT crystals revealed that the Se⋅⋅⋅N chalcogen bond (ChB) in 1 is strong enough to determine the crystal packing with the formation of a cavity suitable for 2,6‐DMN. On the contrary, ChB through S⋅⋅⋅N contact in 2 competes with other weak interactions such as a C−H⋅⋅⋅N hydrogen bond. The stronger ChB involving Se is the key for 1 to separate 2,6‐DMN (>97 wt %) from a complex isomer mixture containing ca. 10 wt % each of 2,6‐ and 2,7‐DMN by a simple, efficient and straightforward mixing‐filtration‐heating process.
- Subjects
CRYSTALS; MOLECULAR recognition; ELECTROPHILES; HYDROGEN bonding
- Publication
European Journal of Organic Chemistry, 2021, Vol 2021, Issue 6, p990
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202001554