2,4,6-tris(azol-1-yl)-1,3,5-triazines: A new class of multidentate ligands

The synthesis of thirteen tris(azol-1-yl)-s-triazines (azole = pyrazoles, i midazoles, 1,2,4-triazole and benzimidazoles) is described. Particularly in teresting are the compounds derived from C-adamantylazoles (4-adamantylpyra zole, 2-adamantylimidazole and 2-adamantylbenzimidazole) because of their h igh lipophilicity. The crystal and molecular structures of 2,4,6-tris(2-phe nylimidazol-1-yl)-1,3,5-triazine (6c) and 2,4,6-tris(2-phenylbenzimidazol-1 -yl)-1,3,5-triazine (8c) have been determined by X-Ray analysis. The molecu lar structure can be described as a propeller taking into account the twist s existing between the central ring and the substituents. The crystal struc ture of both compounds show a distorted hexagonal packing of chains. All tr isazolyltriazines have been fully characterized by H-1-, C-13- and N-15-NMR spectroscopy. The C-13 and N-15 chemical shifts in CDCl3, and trifluoroace tic acid have been used to discuss the conformation and the site of protona tion.