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Issue 20, 2017
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Synthesis and structural characterisation of the aggregates of benzo-1,2-chalcogenazole 2-oxides

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Abstract

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 Te⋯O chalcogen bonding; the structures of the co-crystals with benzene and CH2Cl2 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.

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

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Publication details

The article was received on 18 Feb 2017, accepted on 31 Mar 2017 and first published on 03 Apr 2017


Article type: Paper
DOI: 10.1039/C7DT00612H
Citation: Dalton Trans., 2017,46, 6570-6579
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    Synthesis and structural characterisation of the aggregates of benzo-1,2-chalcogenazole 2-oxides

    P. C. Ho, J. Rafique, J. Lee, L. M. Lee, H. A. Jenkins, J. F. Britten, A. L. Braga and I. Vargas-Baca, Dalton Trans., 2017, 46, 6570
    DOI: 10.1039/C7DT00612H

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