- Mechanically activated solid-phase synthesis of copper(II), zinc(II), and cadmium(II) diethyldithiocarbamates
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The mechanically activated solid-phase reaction of copper, zinc, and cadmium chlorides with sodium diethyldithiocarbamate is studied. The course of the process and the extent of reaction are studied as affected by the parameters of the mechanical activati
- Petrova,Makhaev
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- Fourier Transform Infrared and Raman spectra, DFT: B3LYP/6-311G(d, p) calculations and structural properties of bis(diethyldithiocarbamate)copper(II)
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Theoretical and experimental bands have been assigned for the Fourier Transform Infrared (FT-IR) and FT-Raman spectra of the bis(diethydithiocarbamate)Cu(II) complex, [Cu(DDTC)2]. The calculations and spectra interpretation have been based on the DFT/B3LYP method, infrared and Raman second derivative spectra, and band deconvolution analysis. To better assign the metal-ligand normal modes in the spectral region of low energy, the deviation percentage of the geometrical parameters was used, with values from the interpretation of the normal modes of L matrix. Results indicate a planar structure around the Cu(II) cation. The calculated infrared and Raman spectra, based on the proposed geometrical structure of the bis(diethyldithiocarbamate)copper(II) complex, agreed with the experimental spectra.
- Costa Jr.,Ramos,Tellez Soto,Martin,Raniero,Ondar,Versiane,Moraes
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- Antioxidant potential and secondary reactivity of bisfdiphenyl(2-pyridyl)phosphinogcopper(II) complex
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Copper-based complexes with the general formulas [Cu(L)2]Cl2(1) and [Cu2L2 (μ2-L)μ2-Cl2](2) and a mixed-ligand anionic complex [Cu(L)2 dedtc][LCl] (3b), where L = diphenyl(2-pyridyl)phosphine and dedtc = diethyldithiocarbamate, were synthesized and structurally characterized. X-ray analysis revealed that the coordination environment around the copper atom in complexes 1-3 is distorted tetrahedral. In monomeric complexes 1 and 3b both diphenyl(2-pyridyl) phosphine ligands are monodentate and are coordinated through the P-atom. In complex 3b two phosphine ligands are attached to copper through the P-atom. The third phosphine ligand acts as a bridged ligand, coordinated to the metal centers through the P-atom and N-atom. Complexes 1 and 3b were tested for radical scavenging activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) as a free radical. A prominent color change after mixing the solution of complex 1 and DPPH was observed, indicating the efficiency of the compound as antioxidant.
- Khan, Ezzat,Shahzad, Adnan,Tahir, Muhammad Nawaz,Noor, Awal
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- Stability of diethyl dithiocarbamate chelates with Cu(II), Zn(II) and Mn(II)
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Immobilization has been regarded as one of the most effective technology to eliminate heavy metals contamination. However, the stability of immobilization products and the leakage of immobilized heavy metals impeded its further application. In order to depict the stability of chelating complexes C10H20MnN2S4, C10H20CuN2S4 and C10H20ZnN2S4, DSC-TG analysis, DFT calculation and leakage tests were carried out to reveal the stabilities and the potential leakage risks of immobilized heavy metals when sodium diethyl dithiocarbamate was used as soil amendments. The results indicated that the stability of these three chelating complexes was ranked in the order of C10H20CuN2S4> C10H20ZnN2S4> C10H20MnN2S4. Such precipitations as C10H20MnN2S4, C10H20CuN2S4 and C10H20ZnN2S4 were stable under the neutral and alkaline environment. Meanwhile, leakage of immobilized heavy metals decreased with the increasing leaching pH, whereas time and temperature had no significant impact on the leakage of immobilized heavy metals. And the maximum leakage of immobilized heavy metals was lower than the limited concentration.
- Liu, Wengang,Duan, Hao,Wei, Dezhou,Cui, Baoyu,Wang, Xinyang
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- Disulfiram and Its Copper Chelate Attenuate Cisplatin-Induced Acute Nephrotoxicity in Rats Via Reduction of Oxidative Stress and Inflammation
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The use of cisplatin (CP) in chemotherapy of resistant cancers is limited due to its dose-dependent nephrotoxicity. Disulfiram (DSF), the aversion therapy for alcoholism, has recently emerged as an anticancer and chemopreventive agent. Its anticancer activity is potentiated in the presence of copper. However, such use of copper leads to several adverse effects. In the present study, the protective effect of DSF and its copper chelate (Cu-DEDC) against CP-induced nephrotoxicity in rats was evaluated. Nephrotoxicity was induced by a single intraperitoneal injection of CP (5?mg/kg). The treatment groups included control (vehicle treated), CP (CP-treated), CP + DSF (CP followed by DSF), CP + DSF + Cu (CP followed by DSF and CuCl2), CP + Cu-DEDC (CP followed by Cu-DEDC), and CP + AMF (amifostine pre-treated and CP-treated). The DSF, Cu-DEDC, and CuCl2 were administered orally at 50?mM/kg/day dose for 5?days post CP injection. AMF served as a standard chemo protectant, administered intravenously 30?min prior to CP. The markers of oxidative stress, inflammation, and kidney function estimated on the 6th day revealed that both DSF and Cu-DEDC significantly attenuated the CP-induced rise in the serum/urine creatinine and blood urea nitrogen (BUN). The CP-induced rise in serum alkaline phosphatase (ALPase) was reversed by these drugs. Both drugs reduced the levels of malondialdehyde and nitric oxide (NO) in kidney tissues. These drugs reversed CP-induced depletion of SOD, catalase, and GSH in the kidneys. There was a significant reduction in the CP-induced TNF-α and IL-1β production along with prevention of histological alterations. Above observations indicate that DSF and Cu-DEDC may have significance as adjuvants to protect against CP-induced nephrotoxicity.
- Khairnar, Shraddha I.,Mahajan, Umesh B.,Patil, Kalpesh R.,Patel, Harun M.,Shinde, Sachin D.,Goyal, Sameer N.,Belemkar, Sateesh,Ojha, Shreesh,Patil, Chandragouda R.
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- Magnetic and Structural Studies on Copper(II) Dialkyldithiocarbamates
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The magnetic susceptibilities of a series of copper(II) dialkyldithiocarbamates have been measured over the range 4-290 K, the alkyl groups being methyl, ethyl, isopropyl, and n-butyl.Contrary to a previous report of strong ferromagnetic interaction in the diethyl derivative, we find no evidence of any significant exchange interaction in this compound.The dimethyl and di-isopropyl analogues show weak antiferromagnetic interactions.Only the di-n-butyl derivative in the dialkyl series shows evidence of strong magnetic exchange interaction but of an antiferromagnetic nature; this effect is peculiar to the phase recrystallized from chloroform-light petroleum (α), the phase obtained from chloroform-ethanol (β) showing no such interaction.To seek the origin of the exchange interaction in the α derivative, its crystal structure has been determined by single-crystal X-ray diffraction methods at 295 K and refined by least squares to a residual 0.032 for 1976 'observed' reflections.Crystals are triclinic, P1, a=15.29(1), b=9.963(7), c=9.243(7) Angstroem, α=67.94(7), β=82.92(7), γ=71.55(7) deg, and Z=2.The copper environment is the usual pseudo-square-planar array of four sulphur atoms from two bidentate ligands (, 2.31 Angstroem), but there is a long fifth interaction S, 2.899(4) Angstroem> through the inversion centre leading to pseudo-dimer formation.Although similar to the diethyl analogue in this respect, differences are observed in regard to (a) the bridging geometry in the 'dimer' and (b) the proximity to the 'dimer' sulphur ligands of sulphur atoms from neighbouring dimers at ca. 3.8 Angstroem.The likely relative importance of these two features in determining the origin of the antiferromagnetic coupling is discussed.The structure of the β phase has also been determined, the final residual being 0.036 for 1324 'observed' reflections.Crystals are monoclinic, P21/n, a= 14.593(5), b= 7.840(2), c= 10.822(5) Angstroem, β= 101.55(3) deg, and Z= 2.The molecules are located with the copper atoms on crystallographic centres of symmetry, and the only significant intermolecular interactions observed are SH contacts.The CuS4 entity is planar with 2.30 Angstroem.
- Boyd, Peter D. W.,Mitra, Samaresh,Raston, Colin L.,Rowbottom, Graham L.,White, Allan H.
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- Charge-transfer photochemistry of copper(II) dithiocarbamate mixed-ligand complexes
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The photoredox behaviour of copper(II) diethyldithiocarbamate mixed-ligand complexes, Cu(Et2dtc)X (X = Cl, ClO4, NO3), is characterized by strongly allowed ligand-to-metal charge transfer (LMCT) transition in the visible s
- Jeliazkova,Doicheva
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- Efficient solar light Driven photocatalytic degradation of congo red dye on CdS nanostructures derived from single source precursor
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This article presents a facile synthesis of cadmium sulfide nanorods (CdS-NR) and nanospheres (CdS-NS) using cadmium(II) dithiocarbamate as a precursor in the presence of two different ther-malizing solvents {ethylenediamine (en) and octylamine (OA)}. The as-synthesized CdS-NR and CdS-NS were characterizedby powder X-ray diffraction (PXRD), transmission electron microscopy (TEM), selected area electron diffraction technique (SAED), fourier transmission infrared spectroscopy (FTIR), energy dispersive X-ray spectroscopy (EDS), UV-visible spectroscopy, steady-state and time resolved photoluminesce (PL). TEM analysis has confirmed the formation of nanorods and nanospheres in the presence of en and OA, respectively. The in situ generated different capping ligands, as confirmed by FT-IR analysis, may be responsible for variation in morphology. The XRD results revealed hexagonal (nanorods) and cubic mixed hexagonal phase (nanospheres). Owing to band gapes (UV-Vis) in the visible region, both these nanostructures (nanorods and nanospheres) were tested as a solar light drive photocatalyst for the degradation of Congo red (CR). The results indicated that CdS-NR exhibit better catalytic efficiency (Kapp = 0.366 min?1 toward CR degradation as compared to CdS-NS (Kapp = 0.299 min?1. The better photocatalytic activity of nanorods can be attributed to the anisotropically grown structure which infers longer electron hole recombination time as revealed by the time resolved PL.
- Nasir, Jamal Abdul,Gul, Shaheen,Khan, Azam,Shah, Zawar Hussain,Ahmad, Abrar,Zulfiqar,Khan, Rajwali,Liu, Zhongxin,Chen, Wei,Lin, Dan-Jae,Zia-ur-Rehman
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- On the interaction of copper(ii) with disulfiram
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In combination with copper(ii) ions, disulfiram (DSF) has been reported to be a potentially potent anticancer agent based on in vitro results. The interaction of DSF with copper(ii) chloride in solution has been studied using a range of spectroscopic techniques. There is strong evidence for the rapid formation of the bis(N,N-diethyl dithiocarbamato)copper(ii) complex in situ. Kinetic experiments were used to determine rate laws for the reaction that give insight into the mechanism of the process which may help to explain the observed in vitro cytotoxicity. This journal is
- Lewis, David J.,Deshmukh, Parikshit,Tedstone, Aleksander A.,Tuna, Floriana,O'Brien, Paul
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- Trivalent copper and indium heterometallic complex with dithiocarbamate and iodide ligands
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The heterometallic Cu–In complex salt [Cu(III) (dtc)2][In(III)I4](1) (dtc = S2CNEt2, diethyldithiocarbamate) was prepared by reactions of Cu(II) (dtc)2 and In(III)I3 in benzene solution. As a redox reaction, Cu(II) (dtc)2 was oxidized to [Cu(III) (dtc)2]+, and In(III)I3 was changed to [In(III)I4]?. The square?planar Cu(III)S4 local symmetry of 1 involves a distorted octahedral coordination environment via long?range intermolecular interactions and represents a new one-dimensional structure of [Cu(III) (dtc)2]+ units. The crystal packing system of 1 consists of many [Cu(III) (dtc)2]+ chains surrounded by six parallel chains without solvent molecules. The infrared spectra of 1 showed a higher-frequency C–N thioureide bond in Cu(III) (dtc)2 than that of pristine Cu(II) (dtc)2, which has a lower oxidation state due to the Cu(II) center.
- Lee, Hyun?Jong,Jung, Seonho,Cha, Ji?Hyun,Nam, Dongsik,Choe, Wonyoung,Jung, Duk?Young
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- Alcohol-abuse drug disulfiram targets cancer via p97 segregase adaptor NPL4
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Cancer incidence is rising and this global challenge is further exacerbated by tumour resistance to available medicines. A promising approach to meet the need for improved cancer treatment is drug repurposing. Here we highlight the potential for repurposing disulfiram (also known by the trade name Antabuse), an old alcohol-aversion drug that has been shown to be effective against diverse cancer types in preclinical studies. Our nationwide epidemiological study reveals that patients who continuously used disulfiram have a lower risk of death from cancer compared to those who stopped using the drug at their diagnosis. Moreover, we identify the ditiocarb-copper complex as the metabolite of disulfiram that is responsible for its anti-cancer effects, and provide methods to detect preferential accumulation of the complex in tumours and candidate biomarkers to analyse its effect on cells and tissues. Finally, our functional and biophysical analyses reveal the molecular target of disulfiram's tumour-suppressing effects as NPL4, an adaptor of p97 (also known as VCP) segregase, which is essential for the turnover of proteins involved in multiple regulatory and stress-response pathways in cells.
- Skrott, Zdenek,Mistrik, Martin,Andersen, Klaus Kaae,Friis, S?ren,Majera, Dusana,Gursky, Jan,Ozdian, Tomas,Bartkova, Jirina,Turi, Zsofia,Moudry, Pavel,Kraus, Marianne,Michalova, Martina,Vaclavkova, Jana,Dzubak, Petr,Vrobel, Ivo,Pouckova, Pavla,Sedlacek, Jindrich,Miklovicova, Andrea,Kutt, Anne,Li, Jing,Mattova, Jana,Driessen, Christoph,Ping Dou,Olsen, J?rgen,Hajduch, Marian,Cvek, Boris,Deshaies, Raymond J.,Bartek, Jiri
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- A facile synthesis of Cu(II) diethyldithiocarbamate from monovalent copper-cysteamine and disulfiram
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The copper(II) diethyldithiocarbamate (Cu(DDC)2) complex prepared from disulfiram and Cu(II) species has shown excellent anticancer activity. However, general synthetic methods largely rely on tedious procedures and limited reaction types with undesirable by-products. In this paper, we reported an efficient and atom-economic synthesis of Cu(DDC)2 from disulfiram and monovalent copper cysteamine (Cu(I)Cy) via a one-step oxidation–reduction reaction. Cu(DDC)2 was fully characterized by nuclear magnetic resonance (NMR), mass spectrometry (MS), infrared spectroscopy (IR), scanning electron microscope (SEM), X-ray diffraction (XRD), ultraviolet and visible (UV–Vis) spectrophotometry, X-ray photoelectron spectroscopy (XPS), electron paramagnetic resonance (EPR) and single crystal X-ray diffraction. The proposed reaction mechanism and the effect of reaction conditions on the Cu(DDC)2 synthesis were investigated. The photochemical reactions of Cu(DDC)2 was studied in acetone, DMF, toluene, CCl4, CHCl3 under 254, 365 nm alone or combined 254 & 365 nm irradiation based on UV–vis and EPR measurements. The photolysis rate followed in this order: CCl4 > CHCl3 > DMF > toluene > acetone. The final photolysis products in CHCl3 were DSF and Cu2(DDC)2Cl2.
- Cao, Derong,Chen, Zeliang,Ran, Xueguang,Tang, Hao,Wang, Lingyun
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- Cytotoxicity, anti-microbial studies of M(II)-dithiocarbamate complexes, and molecular docking study against SARS COV2 RNA-dependent RNA polymerase
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Ten transition metal dithiocarbamate (DTC)complexes of the type [M(κ2-Et2DT)2] (1–5), and [M(κ2-PyDT)2] (6–10) (where M?=?Co, Ni, Cu, Pd, and Pt; Et2DT?=?diethyl dithiocarbamate; PyDT?=?pyrrolidine dithiocarbamate) were synthesized and characterized by different methods. The dithiocarbamate acted as bidentate chelating ligands to afford a tetrahedral complexes with Co(II) ion and square planner with other transition metal ions. The dithiocarbamate complexes showed good activity against the pathogen bacteria species. The results showed the Pt-dithiocarbamate complexes are more active against all the tested bacteria than the Pd-dithiocarbamate complex. The dithiocarbamate complexes displayed the maximum inhibition zone against E. coli bacteria, whereas the lowest activity of the dithiocarbamate against Salmonella typhimurium bacteria. The cytotoxicity of the Pd(II) and Pt(II) complexes was screened against the MCF-7 breast cancer cell line and the complexes showed moderate activity compared with the cis-platin. The results indicated that the MCF7 cells treated with 500?μgml of ligands and Pd(II) and Pt(II) complexes after 24 hr exposure showed intercellular space and dead cells. Finally, molecular docking studies were carried out to examine the binding mode of the synthesized compounds against the proposed target; SARS COV2 RNA-dependent RNA polymerase.
- Al-Janabi, Ahmed S. M.,Saleh, Abdulrahman M.,Hatshan, Mohammad R.
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p. 1104 - 1115
(2021/02/20)
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- Leveraging γ-Glutamyl Transferase To Direct Cytotoxicity of Copper Dithiocarbamates against Prostate Cancer Cells
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A prodrug approach is presented to direct copper-dependent cytotoxicity to prostate cancer cells. The prochelator GGTDTC requires activation by γ-glutamyl transferase (GGT) to release the metal chelator diethyldithiocarbamate from a linker that masks its thiol reactivity and metal binding properties. In vitro studies demonstrated successful masking of copper binding as well as clean liberation of the chelator by GGT. GGTDTC was stable to non-specific degradation when incubated with a series of prostate cancer and normal cell lines, with selective release of diethyldithiocarbamate only occurring in cells with measurable GGT activity. The antiproliferative efficacy of the prochelator correlated with cellular GGT activity, with 24 h inhibitory concentrations ranging from 800 nm in prostate cancer lines 22Rv1 and LNCaP to over 15 μm in normal prostate PWR-1E cells. These findings underscore a new strategy to leverage the amplified copper metabolism of prostate cancer by conditional activation of a metal-binding pharmacophore.
- Bakthavatsalam, Subha,Sleeper, Mark L.,Dharani, Azim,George, Daniel J.,Zhang, Tian,Franz, Katherine J.
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supporting information
p. 12780 - 12784
(2018/09/14)
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- Cyclic Voltammetric Studies on some Copper Dithiocarbamates
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Cyclic voltammetry at Pt-electrode in acetone/TBAP has been carried out on Cu(R2dtc)2, Cu(R2dtc)2ClO4 and Cu(R2dtc)2-py ( R = -C2H5, -C3H7 and C6H11) systems.Two redox couples Cu(R2dtc)2+ + e- = Cu(R2dtc)2 and Cu(R2dtc)2 + e- = Cu(R2dtc)2- have been observed in each case.
- Nigam, H. L.,Pandeya, Krishna, B.,Tripathi, I. P.,Shukla, P. R.,Prasad, Jagdish,Srivastava, Krishna
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p. 536 - 540
(2007/10/02)
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- THE DIRECT ELECTROCHEMICAL SYNTHESIS OF DIALKYLDITHIOCARBAMATE AND DIETHYLDITHIOPHOSPHATE COMPLEXES OF MAIN GROUP AND TRANSITION METALS
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Dialkyldithiocarbamate derivatives (R2NCS2)nM of a number of metals (M=Fe, Co, Ni, Cu, Ag, Zn, Cd, In, Tl) have been synthesised in good yield by electrochemical oxidation of appropriate sacrificial anodes in non-aqueous solutions of either the corresponding tetraalkylthiuran disulphide (R2NCS2)2 (R=Me, Et) or a mixture of carbon disulphide plus the secondary amine R2NH (R=Et, i-Pr; R2NH=piperidine).Similar experiments with solutions of (EtO)2P(S)SH (=HL) gave MLn* derivatives (M=Fe, Co, Ni, Cu, Ag, Au, Zn, Cd, Hg, Ga, In, Tl) while in the presence of HL+1,10-phenanthroline, MLn.phen derivatives were obtained for M=V, Mn, Fe, Co, Zn, and Ga.
- Geloso, Corrado,Kumar, Rajesh,Lopez-Grado, Jaime Romero,Tuck, Dennis G.
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p. 928 - 932
(2007/10/02)
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- KINETICS AND MECHANISM OF FORMATION OF COPPER (II) DITHIOCARBAMATES IN ACETONITRILE.
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Kinetics of formation of copper (II) bis-dithiocarbamates in a system, containing copper acetate, diethyl- or dibenzylamine, and carbon disulfide were studied in acetonitrile. Reactions orders in amine (second) and carbon disulfide (first) were determined. Rate constants were determined and it was found that they increase upon addition of pyridine and decrease with an increase in temperature, copper acetate concentration, and upon going from diethyl- to dibenzylamine. The obtained results were explained in the framework of a mechanism, according to which a charge-transfer complex of the amine yields carbon disulfide type is formed at the first stage. Then this complex reacts at the limiting stage with a second amine molecule to give dithiocarbamate ion, which forms rapidly a stable complex with copper ion.
- Maletin,Verkhovlyuk,Sheka
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- Electron Spin Resonance Study of Some Copper(II) Dithiocarbamates and their Mixed-ligand Complexes
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The e.s.r. spectra of seven copper(II) dithiocarbamates have been recorded in chloroform-ethanol mixtures at room temperature and at 113 K.It has been found that the addition of a range of salts to these dithiocarbamates destroys the complex forming a mixed-ligand complex, , with a new e.s.r. spectrum.When X is Cl or Br the additional interaction of the unpaired electron with a single halogen nucleus is observed.The complex forms a dipole-dipole coupled dimer and a computer simulation of the ΔMs = 2 absorption of this dimer has been obtained.
- Newton, William J.,Tabner, Brian J.
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p. 466 - 471
(2007/10/02)
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