Competing Effects of Chlorination on the Strength of Te⋅⋅⋅O Chalcogen Bonds Select the Structure of Mixed Supramolecular Macrocyclic Aggregates of Iso-Tellurazole N-Oxides.
| Autor: | Ho PC; Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, L8S 4 M1, Hamilton, Ontario, Canada., Lomax J; Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, L8S 4 M1, Hamilton, Ontario, Canada., Tomassetti V; Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, L8S 4 M1, Hamilton, Ontario, Canada., Britten JF; Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, L8S 4 M1, Hamilton, Ontario, Canada., Vargas-Baca I; Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, L8S 4 M1, Hamilton, Ontario, Canada. |
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| Jazyk: | angličtina |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2021 Jul 26; Vol. 27 (42), pp. 10849-10853. Date of Electronic Publication: 2021 Jun 09. |
| DOI: | 10.1002/chem.202101425 |
| Abstrakt: | Chlorination of 3-methyl-5-phenyl-1,2-tellurazole-2-oxide yielded the λ 4 Te dichloro derivative. Its crystal structure demonstrates that the heterocycle retains its ability to autoassociate by chalcogen bonding (ChB) forming macrocyclic tetramers. The corresponding Te⋅⋅⋅O ChB distances are 2.062 Å, the shortest observed to date in aggregates of this type. DFT-D3 calculations indicate that while the halogenated molecule is stronger as a ChB donor it also is a weaker ChB acceptor; the overall effect is that the ChBs in the chlorinated homotetramer are not significantly stronger. However, partial halogenation or scrambling selectively yield the 2 : 2 heterotetramer with alternating λ 4 Te and λ 2 Te centers, which calculations identified as the thermodynamically preferred arrangement. (© 2021 Wiley-VCH GmbH.) |
| Databáze: | MEDLINE |
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