Derivatives of the Triaminoguanidinium Ion, 1. Synthesis, Crystal and Molecular Structures of 1,2,3-Tris(benzylamino)guanidinium Salts

Abstract

Triaminoguanidinium chloride was transformed into 1,2,3-tris(benzylamino)guanidinium chloride (3-Cl) in two steps. Anion exchange allowed the preparation of further salts 3-X. The crystal and molecular structures of 3-Cl, 3-I, 3-CF 3 COO and 3-CF 3 SO 3 were determined. It was found that both the conformation of the cation and the nature of the anion determines the packing in the solid state. Interestingly, three different conformations of the cation were observed in the crystals.

Derivatives of the triaminoguanidinium ion, 6. Aminal-forming reactions with aldehydes and ketones

“…Furthermore it should be recalled, that certain 1,2,4,5-tetrazinanes were found to have useful analgesic and antiinflammatory activities [26] and some dihydrotetrazine derivatives [27], in contrast to substituted 1,2,4,5-tetrazinanes [28], exhibited strong antitumor effects. [9] were prepared as reported. Hydrazin-1-yl)-3,3-dimethyl-2,3,4 A chromatographic column (l = 50 cm, diameter 5 cm) was charged with a strongly basic anion exchanger (type III, OH form, Merck Supelco, 4.0 g) dispersed in water (50 mL).…”

“…NMR monitoring revealed that a stepwise dehydrogenation of the three PhCH 2 -NH groups of 10 took place, which finally resulted in tris(benzylidenamino)guanidine 13. The latter can be obtained more conveniently by deprotonation of N,N′,N″-tris(benzylidenamino)guanidinium chloride 14 (which is in fact the direct synthetic precursor of 3-Cl [9]). A crystal structure determination confirmed the identity of 13 (Fig.…”

“…To a solution of N,N′,N″-tris(benzylidenamino)guanidinium chloride (14, 1.76 g. 4.37 mmol) [9] in methanol (40 mL) was gradually added an aqueous solution of NaOH (5 m, 10 mL).…”

“…N,N′,N″-Tris(benzylidenamino)guanidinium salts 3 are easily prepared by catalytic C=N hydrogenation of tris(benzylidenimino)guanidinium salts 2 (R 1 = Ph, R 2 = H) [9]. Some years ago, we started to study the chemistry of salts 3, which in particular were expected to undergo multiple functionalization based on the nucleophilicity of the benzyl-NH nitrogen atom.…”

Computational study of substituent effects on the gas‐phase stabilities of N‐phenylguanidinium ions

“…In the past two decades, ionic liquids (ILs) have attracted much attention and were proposed for a broad range of applications in various areas of natural and engineering sciences . Guanidinium ions constitute a new class of ionic liquids used for various applications . Some authors including one of us have systematically synthesized many hexaalkylguanidinium ionic liquids to investigate their fundamental physicochemical properties as well as to investigate the application to electrochemistry including the development of lithium‐ion batteries .…”