Synthesis and Characterisation of Chiral Triazole-Based Halogen-Bond Donors: Halogen Bonds in the Solid State and in Solution

Mikk Kaasik; Sandra Kaabel; Kadri Kriis; Ivar Järving; Riina Aav; Kari Rissanen; Tõnis Kanger

doi:10.1002/chem.201700618

Synthesis and Characterisation of Chiral Triazole-Based Halogen-Bond Donors: Halogen Bonds in the Solid State and in Solution

Mikk Kaasik, Sandra Kaabel, Kadri Kriis, Ivar Järving, Riina Aav, Kari Rissanen, Tõnis Kanger^*

^*Corresponding author for this work

Not published at Aalto University

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Abstract

A general platform for the synthesis of various chiral halogen-bond (XB) donors based on the triazole core and the characterisation of factors that influence the strength of the halogen bond in the solid state and in solution are reported. The characterisation of XB donors in the solid state by X-ray crystallography and in solution by ¹H NMR titration can be used to aid the design of new XB donors. We describe the first example of a XB between iodotriazoles and thioureas in solution. In addition, the enantiodiscrimination of acceptors in solution through halogen-bond participation is described.

Original language	English
Pages (from-to)	7337-7344
Number of pages	8
Journal	Chemistry - A European Journal
Volume	23
Issue number	30
DOIs	https://doi.org/10.1002/chem.201700618
Publication status	Published - 29 May 2017
MoE publication type	A1 Journal article-refereed

Keywords

donor–acceptor systems
halogen bonds
heterocycles
NMR titrations
X-ray diffraction

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AU - Aav, Riina

AU - Rissanen, Kari

AU - Kanger, Tõnis

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Synthesis and Characterisation of Chiral Triazole-Based Halogen-Bond Donors: Halogen Bonds in the Solid State and in Solution

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Keywords

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