Maugeri, L;
Asencio-Hernández, J;
Lébl, T;
Cordes, DB;
Slawin, AMZ;
Delsuc, M-A;
Philp, D;
(2016)
Neutral iodotriazoles as scaffolds for stable halogen-bonded assemblies in solution.
Chemical Science
, 7
(10)
pp. 6422-6428.
10.1039/C6SC01974A.
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Abstract
The halogen bond (XB) donor properties of neutral 1,4-diaryl-5-iodo-1,2,3-triazoles are explored using a combination of computational and experimental results and are shown to be competitive in halogen bonding efficiency with the classic pentafluoroiodobenzene XB donor. The SNAr reactivity of these donors permits the facile assembly of an iodotriazole functionalised with a 3-oxypyridine XB acceptor, thus generating a molecular scaffold capable of undergoing dimerisation through the formation of two halogen bonds. The formation of this halogen-bonded dimer is demonstrated by 1H and DOSY NMR experiments and a plausible structure generated using DFT calculations.
Type: | Article |
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Title: | Neutral iodotriazoles as scaffolds for stable halogen-bonded assemblies in solution |
Open access status: | An open access version is available from UCL Discovery |
DOI: | 10.1039/C6SC01974A |
Publisher version: | http://dx.doi.org/10.1039/C6SC01974A |
Language: | English |
Additional information: | This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (https://creativecommons.org/licenses/by/3.0/) |
UCL classification: | UCL UCL > Provost and Vice Provost Offices UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences |
URI: | https://discovery.ucl.ac.uk/id/eprint/10057744 |
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