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

Research output: Contribution to journalArticleScientificpeer-review

44 Citations (Scopus)

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 languageEnglish
Pages (from-to)7337-7344
Number of pages8
JournalChemistry - A European Journal
Volume23
Issue number30
DOIs
Publication statusPublished - 29 May 2017
MoE publication typeA1 Journal article-refereed

Keywords

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

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