Copper Complexes of 1,4-Naphthoquinone Containing Thiosemicarbazide and Triphenylphosphine Oxide Moieties; Synthesis and Identification by NMR, IR, Mass, UV Spectra, and DFT Calculations

Abstract

New 1,4-naphthoquinone derived by triphenylphosphaneylidene (Ph 3 P) and N -substituted-hydrazine-1-carbothioamides were obtained during a one-pot reaction of 2,3-dichloro-1,4-naphthoquinone with thiosemicarbazides, Ph 3 P and in the presence of triethyl amine (Et 3 N) as a catalyst. The structure of the ligands was established by ESI, IR, and NMR spectra, in addition to elemental analyses and X-ray structure analysis. On subjecting the newly prepared ligands with CuCl 2 and Ph 3 P, autoxidation occurs, and ( E )-(2-(1,4-dioxo-3-(triphenyl phosphanylidene)-3,4-dihydronaphthalen-2(1 H )-ylidene)carbamothioyl)hydrazinyl)-((triphenylphosphanyl)oxy)copper derivatives were formed in very good yields. The structure of the obtained complexes was proved by ESI, IR, NMR, and UV spectra, in addition to elemental analyses and theoretical calculations.

Transition Metal Complexes of Thiosemicarbazides, Thiocarbohydrazides, and Their Corresponding Carbazones with Cu(I), Cu(II), Co(II), Ni(II), Pd(II), and Ag(I)—A Review

“…Thiosemicarbazones derived by 1,4-naphthoquinone 29a – f were established upon mixing equimolar amounts of thiosemicarbazides 11e – j with 2,3-dichloro-1,4-naphthoquinone ( 28 ), Ph 3 P and in the presence of Et 3 N as a catalyst and acetonitrile as a solvent. Triphenylphosphine-ylidene)-3,4-dihydronaphthalen-2(1 H )-ylidene)- N -substituted-hydrazine-1-carbothioamides 29a – f were obtained in 72–82% yield ( Scheme 13 ) [ 63 ].…”

“…Recently Aly et al [ 63 ] reported that the reaction of equal equivalents of compounds 29a – f with Ph 3 P and CuCl 2 .2H 2 O in ethanol at rt and for 1–3 d produced the bidentate Cu-complexes 54a – f in 80–93% yields as indicated in Scheme 26 .…”

Selective extraction of silver(I) and photometric determination di-(2-naphthyl)-thiocarbazone (dinaftizone) in the organic phase

“…Despite a fairly large number of methods, problems in determining silver in various objects remain. This is explained, first of all, by increased requirements for the quality of the results of such analyzes, as well as by the complexity of most silver-containing samples [3][4][5]. It is known that in many natural and industrial samples, silver is found in ultra-small quantities against the background of large quantities of copper, nickel, cobalt, iron, cadmium and others that are quite similar in chemical properties.…”