Synthesis and structural characterisation of the aggregates of benzo-1,2-chalcogenazole 2-oxides

Iodine oxidation of bis[2-(hydroxyiminomethyl)phenyl] dichalcogenides yields benzo-1,2-chalcogenazole 2-oxides. Annulated derivatives of iso-tellurazole N-oxides spontaneously aggregate into cyclic tetra- and hexamers through TeO chalcogen bonding; the structures of the co-crystals with benzene and...

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Published inDalton transactions : an international journal of inorganic chemistry Vol. 46; no. 20; pp. 6570 - 6579
Main Authors Ho, Peter C, Rafique, Jamal, Lee, Jiwon, Lee, Lucia M, Jenkins, Hilary A, Britten, James F, Braga, Antonio L, Vargas-Baca, Ignacio
Format Journal Article
LanguageEnglish
Published England 23.05.2017
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Summary:Iodine oxidation of bis[2-(hydroxyiminomethyl)phenyl] dichalcogenides yields benzo-1,2-chalcogenazole 2-oxides. Annulated derivatives of iso-tellurazole N-oxides spontaneously aggregate into cyclic tetra- and hexamers through TeO chalcogen bonding; the structures of the co-crystals with benzene and CH Cl illustrate the ability of these macrocycles to interact with small guest molecules. The selenium congener crystallizes forming a supramolecular polymer. VT NMR indicates that both compounds aggregate in solution but only at low temperature in the selenium case. The different abilities of these molecules to engage in supramolecular interactions are interpreted on the basis of their electronic properties evaluated with DFT-D3 calculations.
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ISSN:1477-9226
1477-9234
DOI:10.1039/c7dt00612h