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, HL¹, C₁₂H₂₂N₂OS, crystallizes in the orthorhombic space group P2₁2₁2₁, with Z = 4, and unit cell parameters, a = 6.6925(13) Å, b = 9.0457(18) Å, c = 22.728(5) Å. The conformation of the HL¹ 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°, −67.47° and 115.50°, respectively. The structure of HL¹ also shows a delocalization of the π 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(L⁵)₂, C₂₄H₃₈N₄NiO₄S₂, crystallizes in the monoclinic space group P2₁/c, with Z = 4, and unit cell parameters, a = 16.919(3) Å, b = 8.3659(17) Å, c = 19.654(4) Å, β = 107.43(3)°. Ni(L⁵)₂ is a cis-complex with a slightly distorted square-planar coordination of the central nickel by two oxygen and two sulfur atoms.

Keywords:

• Synthesis
• Thiourea
• Cyclohexanecarboxamide
• Complex
• Single crystal structure

Acknowledgement

This work was supported by Mersin University Research Fund (Project No.: BAP-SBE TB (CKÖ) 2007-1).