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 Fossey
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.
Topics & Concepts
Axial chiralityArylChirality (physics)TriazoleAtropisomerEnantiomer1,2,3-TriazoleMoleculeRotation (mathematics)ChemistryAxial symmetryCombinatorial chemistryStereochemistryCrystallographyEnantioselective synthesisMathematicsPhysicsGeometryOrganic chemistryCatalysisAlkylNambu–Jona-Lasinio modelQuarkQuantum mechanicsChiral symmetry breakingAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityCarbohydrate Chemistry and Synthesis