Enantiomer stability of atropisomeric 1,5-disubstituted 1,2,3-triazoles

Fernanda Meloni, William D.G. Brittain, Louise Male, Cécile S. Le Duff, Benjamin R. Buckley, Andrew G. Leach, John S. Fossey

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Abstract

The synthesis and characterisation of axially chiral atropisomeric 1,5-disubstituted 1,2,3-triazoles is reported. Molecules designed to display restricted rotation about 1,2,3-triazole N-1-aryl or 1,2,3-triazole C-5-aryl bonds were investigated by physical and computational techniques. The barrier to 1,2,3-triazole N-1-aryl rotation was found to be higher than that for 1,2,3-triazole C-5-aryl rotation, confirming axial chirality stemming from restricted rotation about an N-1-aryl bond in a 1,5-disubstituted 1,2,3-triazole to be the most suitable for the development of an axial chirality triazole-based platform.
Original languageEnglish
Article number100004
Number of pages14
JournalTetrahedron Chem
Volume1
Early online date11 Dec 2021
DOIs
Publication statusPublished - Mar 2022

Keywords

  • Chirality
  • Atropisomer
  • Axial chirality
  • Triazole
  • Click chemistry
  • Crystal Structure
  • Computational chemistry

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