Substituent effect on the formation of helical to layered hydrogen bond networks in hydroxyl and carboxyl substituted 1-aryl-1H-1,2,3-triazoles

Abstract

Six structurally related 1-aryl-1H-1,2,3-triazoles substituted with hydroxyl and carboxyl groups have been studied by single crystal X-ray crystallography. O–H⋯N and O–H⋯O hydrogen bond synthons play a predominant role in the crystal engineering of these derivatives. The positions of the hydroxyl and carboxyl groups are important and have an effect on the dihedral angle of the twisted conformations of these molecules in the solid state which in turn dictates the formation of helical or layered hydrogen bond motifs and the chirality of the crystals.