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

descriptionPublicationkeyboard_double_arrow_right Article 25 Oct 2021 United Kingdom Publisher:American Chemical Society (ACS)Journal:Tetrahedron Chem, volume 1, page 100,004 (issn: 2666-951X,

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

doi: 10.26434/chemrxiv-2021-znd87 , 10.1016/j.tchem.2021.100004

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

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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.

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United Kingdom

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Keywords

QD241-441, Click chemistry, Atropisomer, Crystal Structure, Organic chemistry, Triazole, Chirality, Axial chirality

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