Halide ion recognition via chalcogen bonding in the solid state and in solution. Directionality and linearity

Group 16 chalcogen atoms may exhibit Lewis acidic σ-holes which are able to form attractive supramolecular interactions with Lewis bases via chalcogen bonds (ChB). Interest in ChB is increasing rapidly; however, the potential for anion binding has not been fully explored. Herein we report on the app...

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Bibliographic Details
Published in:CrystEngComm 2018, Vol.20 (41), p.6406-6411
Main Authors: Kumar, Vijith, Leroy, César, Bryce, David L.
Format: Article
Language:English
Subjects:
Chalcogen bonds
Chemical bonds
Computational chemistry
Covalent bonds
Crystal structure
Crystallography
Linearity
NMR spectroscopy
Organic chemistry
Recognition
Selenium
Single crystals
Solid state
Structural analysis
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Summary:Group 16 chalcogen atoms may exhibit Lewis acidic σ-holes which are able to form attractive supramolecular interactions with Lewis bases via chalcogen bonds (ChB). Interest in ChB is increasing rapidly; however, the potential for anion binding has not been fully explored. Herein we report on the application of chemically robust and stable benzylic selenocynates ( 1 and 2 ) for halide ion recognition in the solid state and in solution. Single crystal X-ray structural analysis of various cocrystals reveals structurally important Se⋯X − (X = Cl, Br, I) chalcogen bonds. Changes in the 13 C and 77 Se chemical shifts via NMR spectroscopy show how halide ion recognition influences the local electronic environment of the selenium atoms in solution. Deviations of the interaction from the extension of the C–Se covalent bond are quantified and assessed with the aid of computational chemistry.
ISSN:1466-8033
1466-8033
DOI:10.1039/C8CE01365A