Solid-state tubular assemblies of thiolactones: synthesis and structural characterization (CROSBI ID 120433)
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Vujasinović, Ines ; Veljković, Jelena ; Mlinarić-Majerski, Kata ; Molčanov, Krešimir ; Kojić-Prodić, Biserka
engleski
Solid-state tubular assemblies of thiolactones: synthesis and structural characterization
The synthesis of cyclic thiolactones, 2, 5, 8-trithiacyclododecane-1, 9-dione (4), 2, 5, 8, 14, 17, 20-hexathiacyclotetracosane-1, 9, 13, 21-tetraone (5), 2, 5, 8-trithiacyclotetradecane-1, 9-dione (6) and 2, 5, 8, 16, 19, 22-hexathiacyclooctacosane-1, 9, 15, 23-tetraone (7) was achieved by tin-template reaction of 2, 2-dibutyl-2-stanna-1, 3, 6-trithiacyclooctane (1) with corresponding diacyl chlorides. The structures of 12-, 14-, 24- and 28-membered ring systems of 4, 6, 5, and 7, respectively, were investigated by X-ray structure analysis. These investigations revealed that, in the solid state, thiolactones 4 and 7 form tubular assemblies. However, the crystal structure of 5 forms layered packing dominated by CH...O hydrogen bonds whereas 6 forms three-dimensional network via CH...O hydrogen bonds and van der Waals interactions.
di-polythiolactones ; tetra-polythiolactones ; cyclization ; tubular structures
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