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

doi:10.1016/j.tchem.2021.100004

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

Chemistry

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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 language	English
Article number	100004
Number of pages	14
Journal	Tetrahedron Chem
Volume	1
Early online date	11 Dec 2021
DOIs	https://doi.org/10.1016/j.tchem.2021.100004
Publication status	Published - Mar 2022

Keywords

Chirality
Atropisomer
Axial chirality
Triazole
Click chemistry
Crystal Structure
Computational chemistry

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

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.",

keywords = "Chirality, Atropisomer, Axial chirality, Triazole, Click chemistry, Crystal Structure, Computational chemistry",

author = "Fernanda Meloni and Brittain, {William D.G.} and Louise Male and Duff, {C{\'e}cile S. Le} and Buckley, {Benjamin R.} and Leach, {Andrew G.} and Fossey, {John S.}",

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month = mar,

doi = "10.1016/j.tchem.2021.100004",

language = "English",

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TY - JOUR

T1 - Enantiomer stability of atropisomeric 1,5-disubstituted 1,2,3-triazoles

AU - Meloni, Fernanda

AU - Brittain, William D.G.

AU - Male, Louise

AU - Duff, Cécile S. Le

AU - Buckley, Benjamin R.

AU - Leach, Andrew G.

AU - Fossey, John S.

PY - 2022/3

Y1 - 2022/3

N2 - 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.

AB - 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.

KW - Chirality

KW - Atropisomer

KW - Axial chirality

KW - Triazole

KW - Click chemistry

KW - Crystal Structure

KW - Computational chemistry

U2 - 10.1016/j.tchem.2021.100004

DO - 10.1016/j.tchem.2021.100004

M3 - Article

VL - 1

JO - Tetrahedron Chem

JF - Tetrahedron Chem

M1 - 100004

ER -

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

Abstract

Keywords

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