TY - UNPB
T1 - Enantiomer stability of atropisomeric 1,5-disubstituted 1,2,3-triazoles
AU - Meloni, Fernanda
AU - Brittain, William
AU - Male, Louise
AU - Duff, Cécile Le
AU - Buckley, Benjamin
AU - Leach, Andrew
AU - Fossey, John
PY - 2021/10/25
Y1 - 2021/10/25
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.
U2 - 10.33774/chemrxiv-2021-znd87
DO - 10.33774/chemrxiv-2021-znd87
M3 - Preprint
BT - Enantiomer stability of atropisomeric 1,5-disubstituted 1,2,3-triazoles
PB - ChemRxiv
ER -