Synthesis and crystal structures of three new benzotriazolylpropanamides

Abstract

The crystal structures of benzotriazolylpropanamides are governed by π–π stacking between the benzotriazolyl residues and, in the case of primary amide NH2 groups, by N—H⋯O and N—H⋯N bridging.

A Polymorphic Gold(III) Complex Comprising a Multifunctional Triazolylpropanamide Ligand

“…Consequently, the hydrogen bonding pattern in 2b is different than in 2a , including N–H ··· N bonds and uninvolved amide O atoms (Scheme c). In most of the previously reported related compounds, N–H ··· O bonds are preferred over N–H ··· N bonds . Direct attractive Au ··· Au interactions are again of minor relevance in 2b , as the shortest intermetallic distance is approx.…”

“…Like all previously reported preparations of transition metal complexes with pyrazolylpropanamide-derived ligands, [31][32][33][34] , the reaction of HAuCl 4 •4H 2 O with 1 was carried out in ethanol solution in the presence of triethylorthoformate, HC(OEt) 3 , as dehydrating agent (Scheme 1). Solutions of the starting materials in ethanol were combined and left to stand undisturbed for several days.…”

“…In most of the previously reported related compounds, N-H•••O bonds are preferred over N-H•••N bonds. [31][32][33][34] We also determined the crystal structure of the hydrochloride 3. Herein, the 4-position of the triazolyl ring is protonated, which indicates again that this N atom is more basic than the N atom in 2-position.…”

“…Coordination of the PPA ligand to first‐ and second‐row transition metals allowed the design of a variety of hydrogen bonded supramolecular assemblies, including different chains, sheets, and three‐dimensional arrays . A significant advantage of the PPA ligand system is that it can be easily modified either by attachment of substituents to the propanamide backbone or by replacing the pyrazole ring by other N‐heterocycles such as triazole, or benzotriazole . Thus far, 3‐(1 H ‐1,2,4‐triazol‐1‐yl)propaneamide ( 1 , TPA) has been used only in combination with the first‐row transition metals Mn and Fe .…”