Transition Metal Promoted Addition of Methanol to Cyanoguanidine. Molecular Structure and Properties of the Generated Copper(II) and Nickel(II) Complexes

Abstract

The reaction of the Cu II and Ni II complexes of saccharin with dicyandiamide (cyanoguanidine, cnge) in methanol produces the addition of methanol to the nitrile moiety of this molecule. Furthermore, the product of the reaction coordinates the metal centers generating two new complexes containing saccharinate as the counter anion. The crystal structures of [Cu(cnge-OCH 3 ) 2 ]-(sac) 2 and of [Ni(cnge-OCH 3 ) 2 ](sac) 2 ·2H 2 O (cnge-OCH 3 ϭ 1-amidino-O-methylurea) were solved by single crystal X-ray diffractome-

Molecular structure, bioavailability and bioactivity of [Cu(o-phen)2(cnge)](NO3)2·2H2O and [Cu(o-phen)(cnge)(H2O)(NO3)2] complexes

“…H (41) H (42) H (32) H (31) Some transition metal ions (cf. copper, platinum and nickel) are able to catalyze the addition of alcohols to the nitrile group in cnge, forming n-alkylguanylureas that coordinates the metal ions [13][14][15][16]. The formation of copper complexes of cyanoguanidine has been reported earlier, and they were structurally characterized.…”

PdII‐Promoted Single‐Pot Template Transformations of Benzonitriles, Cyanoguanidine and Sodium Dicyanamide with the Formation of Symmetrical and Asymmetrical (1,3,5‐Triazapentadienate)palladium(II) Complexes

“…For the preparation of asymmetrical 2-amino-4-alkoxy-1,3,5-triazapentadienate-Pd II complexes, a modified onepot template synthesis that was reported for the methanolcyanoguanidine integration at Pt II , [19] Ni II and Cu II [20] centers was employed. Thus, treatment of PdCl 2 with 2 equiv.…”

“…[17][18][19][20] Until now only copper, nickel and platinum ions have been studied in these transformation reactions and no data on palladium(II)-mediated transformations have been reported, irrespective of the potential ability of Pd II to form tap complexes [3,5,6,10,12,16] and its expected behavioural similarity to that of Pt II in promoting nucleophilic addition reactions with substrates containing the CϵN group, namely organonitriles. [24][25][26][27] Thus, one can conclude that the template conversions of CϵN-containing reagents to tap ligands bound to Pd II cen-ters deserve to be explored further as a convenient route to new tap-palladium(II) complexes.…”

“…[3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] These compounds are triaza isoelectronic analogues of the well known and widely used O,O-β-diketonates R-C(=O)-CH-C(=O)-R, and usually coordinate to a metal ion as chelating N,Nbidentate ligands, forming stable complexes with a square planar core. [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] On the other hand, it was noted [9] that these ligands resemble bis(pyrazolyl)borates, another important class of ligands. Thus, tap can also potentially impact areas in which O,O-β-diketonates or bis(pyrazolyl)borates find application, such as in organic synthesis, catalysis, the preparation of optical recording materials, enzyme inhibition, analytical chemistry, etc.…”

Measurement, correlation of the solubility and solution thermodynamics of 2-cyanoguanidine in (methanol+water) binary solvent systems from T=(283.15 to 343.15)K

“…2-Cyanoguanidine is also named dicyandiamide, which is widely used as a significant organic intermediate for many fields, including the production of pharmaceuticals, printing and dying [1][2][3][4]. It is also used as the raw material for coating [5].…”