Synthesis and characterization of N -(alky(aryl)carbamothioyl)cyclohexanecarboxamide derivatives and their Ni(II) and Cu(II) complexes

Abstract

N-(R-carbamothioyl)cyclohexanecarboxamides (R: diethyl, di-n-propyl, di-n-butyl, diphenyl and morpholine-4) and their Ni(II) and Cu(II) complexes have been synthesized and characterized by elemental analyses, FT-IR and NMR methods. N-(diethylcarbamothioyl) cyclohexanecarboxamide, HL 1 , C 12 H 22 N 2 OS, crystallizes in the orthorhombic space group P2 1 2 1 2 1 , with Z ¼ 4, and unit cell parameters, a ¼ 6.6925(13) Å , b ¼ 9.0457(18) Å , c ¼ 22.728(5) Å . The conformation of the HL 1 molecule with respect to the thiocarbonyl and carbonyl moieties is twisted, as reflected by the torsion angles O1-C6-N2-C5, C6-N2-C5-N1 and S1-C5-N2-C6 of 1.68 , À67.47 and 115.50 , respectively. The structure of HL 1 also shows a delocalization of the electrons of the thiocarbonyl group over the C-N bonds. The ring puckering analysis shows that the cyclohexane ring has a chair conformation. The bis(N-(morpholine-4-carbonothioyl)cyclohexane carboxamido)nickel(II) complex, Ni(L 5 ) 2 , C 24 H 38 N 4 NiO 4 S 2 , crystallizes in the monoclinic space group P2 1 /c, with Z ¼ 4, and unit cell parameters, a ¼ 16.919(3) Å , b ¼ 8.3659(17) Å , c ¼ 19.654(4) Å , ¼ 107.43(3) . Ni(L 5 ) 2 is a cis-complex with a slightly distorted square-planar coordination of the central nickel by two oxygen and two sulfur atoms.

Crystal Structure and Cyclic Voltammetric Studies on the Metal Complexes of N-(Dimethylcarbamothioyl)-4-fluorobenzamide

“…The ] C=O stretching vibration can be observed in the ligand at 1695 cm −1 , and the ] CO stretching vibration of the corresponding Ni(II) and Cu(II) complexes appears at 1445 and 1493 cm −1 , respectively. This is in close agreement with other previously studied thiourea derivatives [18,19,29,[32][33][34][35].…”

“…Complex compounds were prepared according to the method described in literature [18,19,29,32,33]. A metal acetate solution in methanol was added dropwise to the ligand in a 1 : 2 molar ratio in methanol.…”

“…Due to these properties, the studies on the electrochemical properties of benzoyl thiourea derivatives are found in literature, albeit to a lesser extent [20][21][22][23][24][25][26][27][28]. The presence of hard O-and N-and soft S-donor atoms in the backbones of these ligands enables them to react readily with both, transition group and main group metal ions, yielding stable metal complexes [29]. The present paper reports the synthesis, characterization, and electrochemical properties on copper(II) and nickel(II) complexes of N-(dimethylcarbamothioyl)-4-fluorobenzamide compounds.…”

Crystal structure of cis-copper(II) complex with N-(di-n-propylcarbamothioyl)cyclohexanecarboxamide ligand

“…The ligand was prepared according to procedure reported in the literature [24]. A solution of cyclohexanecarbonyl chloride (0.005 mole) in acetone (30 mL) was added dropwise to a suspension of potassium thiocyanate (0.005 mole) in acetone (30 mL).…”

Synthesis, characterization and crystal structure of cis-bis[4-fluoro-N-(diethylcarbamothioyl)benzamido-κ2O,S]platinum(II)

“…Thioureabased compounds are good candidates for coordination to transition metals as they have sulfur and oxygen donor atoms [13,[23][24][25][26][27][28][29][30]. They are also able to bind through multiple bonding modes with one metal ion: chelation through both S and O, just through S, or just through O atoms [31]. Thioureas are selective ligands for the platinum group metals such as rhodium, platinum and palladium [32].…”