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- Title
Halogen Bond-Assisted Supramolecular Dimerization of Pyridinium-Fused 1,2,4-Selenadiazoles via Four-Center Se 2 N 2 Chalcogen Bonding.
- Authors
Dukhnovsky, Evgeny A.; Novikov, Alexander S.; Kubasov, Alexey S.; Borisov, Alexander V.; Sikaona, Nkumbu Donovan; Kirichuk, Anatoly A.; Khrustalev, Victor N.; Kritchenkov, Andreii S.; Tskhovrebov, Alexander G.
- Abstract
The synthesis and structural characterization of α-haloalkyl-substituted pyridinium-fused 1,2,4-selenadiazoles with various counterions is reported herein, demonstrating a strategy for directed supramolecular dimerization in the solid state. The compounds were obtained through a recently discovered 1,3-dipolar cycloaddition reaction between nitriles and bifunctional 2-pyridylselenyl reagents, and their structures were confirmed by the X-ray crystallography. α-Haloalkyl-substituted pyridinium-fused 1,2,4-selenadiazoles exclusively formed supramolecular dimers via four-center Se···N chalcogen bonding, supported by additional halogen bonding involving α-haloalkyl substituents. The introduction of halogens at the α-position of the substituent R in the selenadiazole core proved effective in promoting supramolecular dimerization, which was unaffected by variation of counterions. Additionally, the impact of cocrystallization with a classical halogen bond donor C6F3I3 on the supramolecular assembly was investigated. Non-covalent interactions were studied using density functional theory calculations and topological analysis of the electron density distribution, which indicated that all ChB, XB and HB interactions are purely non-covalent and attractive in nature. This study underscores the potential of halogen and chalcogen bonding in directing the self-assembly of functional supramolecular materials employing 1,2,4-selenadiazoles derived from recently discovered cycloaddition between nitriles and bifunctional 2-pyridylselenyl reagents.
- Subjects
RING formation (Chemistry); DIMERIZATION; HALOGENS; ELECTRON density; ELECTRON distribution; X-ray crystallography
- Publication
International Journal of Molecular Sciences, 2024, Vol 25, Issue 7, p3972
- ISSN
1661-6596
- Publication type
Article
- DOI
10.3390/ijms25073972