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Neutral iodotriazoles as scaffolds for stable halogen-bonded assemblies in solution

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Philp_2016_ChemSci_Iodotriazoles_CC.pdf (1.718Mb)
Date
01/10/2016
Author
Maugeri, Leonardo
Asencio-Hernández, Julia
Lebl, Tomas
Cordes, David Bradford
Slawin, Alexandra Martha Zoya
Delsuc, Marc-André
Philp, Douglas
Keywords
QD Chemistry
NDAS
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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.
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
DOI
https://doi.org/10.1039/C6SC01974A
ISSN
2041-6520
Type
Journal article
Rights
This is an Open Access article, which is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/9074

Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.

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