Neutral iodotriazoles as scaffolds for stable halogen-bonded assemblies in solution
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.
Citation
Maugeri , L , Asencio-Hernández , J , Lebl , T , Cordes , D B , Slawin , A M Z , Delsuc , M-A & Philp , D 2016 , ' Neutral iodotriazoles as scaffolds for stable halogen-bonded assemblies in solution ' , Chemical Science , vol. 7 , no. 10 , pp. 6422-6428 . https://doi.org/10.1039/C6SC01974A
Publication
Chemical Science
Status
Peer reviewed
ISSN
2041-6520Type
Journal article
Rights
This is an Open Access article, which is licensed under a Creative Commons Attribution 3.0 Unported Licence.
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