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

Leonardo Maugeri; Julia  Asencio-Hernández; Tomas Lebl; David Bradford Cordes; Alexandra Martha Zoya Slawin; Marc-André Delsuc; Douglas Philp

doi:10.1039/C6SC01974A

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

Leonardo Maugeri, Julia Asencio-Hernández, Tomas Lebl, David Bradford Cordes, Alexandra Martha Zoya Slawin, Marc-André Delsuc, Douglas Philp

Research output: Contribution to journal › Article › peer-review

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 S_NAr 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.

Original language	English
Pages (from-to)	6422-6428
Number of pages	7
Journal	Chemical Science
Volume	7
Issue number	10
Early online date	23 Jun 2016
DOIs	https://doi.org/10.1039/C6SC01974A
Publication status	Published - 1 Oct 2016

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10.1039/C6SC01974ALicence: CC BY

Philp_2016_ChemSci_Iodotriazoles_CC
This is an Open Access article, which is licensed under a Creative Commons Attribution 3.0 Unported Licence.
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EU FP7 Marie Curie ITN READ: Marie Curie ITN 'READ'
Philp, D. (PI)
European Commission
1/02/08 → 31/01/11
Project: Standard

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title = "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. ",

author = "Leonardo Maugeri and Julia Asencio-Hern{\'a}ndez and Tomas Lebl and Cordes, {David Bradford} and Slawin, {Alexandra Martha Zoya} and Marc-Andr{\'e} Delsuc and Douglas Philp",

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doi = "10.1039/C6SC01974A",

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T1 - Neutral iodotriazoles as scaffolds for stable halogen-bonded assemblies in solution

AU - Maugeri, Leonardo

AU - Asencio-Hernández, Julia

AU - Lebl, Tomas

AU - Cordes, David Bradford

AU - Slawin, Alexandra Martha Zoya

AU - Delsuc, Marc-André

AU - Philp, Douglas

PY - 2016/10/1

Y1 - 2016/10/1

N2 - 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.

AB - 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.

U2 - 10.1039/C6SC01974A

DO - 10.1039/C6SC01974A

M3 - Article

SN - 2041-6520

VL - 7

SP - 6422

EP - 6428

JO - Chemical Science

JF - Chemical Science

IS - 10

ER -

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

Abstract

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