The spectral and magnetic properties of copper(II)cyanoacetate

Wasson, John R.; Shyr, Chin‐I; Trapp, Charles

doi:10.1021/ic50061a017

Cited by 146 publications

(49 citation statements)

References 30 publications

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“…are listed in Table 1. By reaction of CuA2.4H20 It agrees with that observed in other carboxylate with bases the water molecules can be replaced complexes (13,19). The observed v(NH)(") and to give compounds of the type CuA,B (B = pz, v(CO)(") bands of N-acetylglycine after coordinaphen, bipy) and CuA,B, (B = CH,-pz, pd, mf, tion exclude the coordination of these groups py, en).…”

Section: Cua24h2o (1 MMI Treating With Ethyl Ether Andsupporting

confidence: 82%

“…In view of the relative insolubility, low magreported in (12) and other similar compounds (12,13). The solid C u A 2 4 H 2 0 complex exhibits normal paramagnetic behavior and has an electronic spectrum similar to that observed for copper(1I) hippurate dimer 420), which is consistent with a distorted square-pyramidal field and a coordination sphere of five bonded oxygen atoms (20).…”

Section: Cua24h2o (1 MMI Treating With Ethyl Ether Andmentioning

confidence: 75%

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Preparation, Infrared Spectra, Electronic Spectra, and Magnetic Moments of Copper(II) Complexes of N-Acetylglycine and Their Amine Adducts

Marcotrigiano¹,

Pellacani²

1974

Can. J. Chem.

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Compounds of the type [CuA2•H2O]2 and [CuA2•4H2O]2 have been prepared, where A is N-acetylglycine (aceturic acid). Amine adducts of the type CuA2B (B = piperazine, 2,2′-bipyridine, and 1,10-phenantroline) and CuA2B2 (B = N-methylpiperazine, piperidine, morpholine, pyridine, and ethylenediamine) were obtained by reaction of the amines with CuA2•4H2O. Each complex was characterized by elemental analysis, infrared spectrum, electronic spectrum, and magnetic moment. For the piperazine and ethylenediamine adducts a square-planar pattern of coordination about copper(II) ion is probable, while for the other amine adducts a square-pyramidal structure is proposed. For all the complexes the coordination of the N-acetylglycine occurs only through the terminal carboxyl oxygen in a monodentate arrangement.

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Section: Cua24h2o (1 MMI Treating With Ethyl Ether Andsupporting

confidence: 82%

Section: Cua24h2o (1 MMI Treating With Ethyl Ether Andmentioning

confidence: 75%

Preparation, Infrared Spectra, Electronic Spectra, and Magnetic Moments of Copper(II) Complexes of N-Acetylglycine and Their Amine Adducts

Marcotrigiano¹,

Pellacani²

1974

Can. J. Chem.

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“…15. Several examples of ESR involving two interacting S = 1 metalslhave appeared in the literature (15)(16)(17)(18)(19)(20)(21)(22). Calculated distances have been in agreement with x-ray crystal structures where available (15,16).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of "face-to-face" porphyrins.

Collman¹,

Elliott²,

Halbert³

et al. 1977

Proc. Natl. Acad. Sci. U.S.A.

135

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The syntheses of four binary porphyrins, two of which are constrained to a "face-to-face" conformation, and their Co2+ and Cu2+ derivatives are described. Electron spin resonance indicates that the intermetallic separation in the binuclear "face-to-face" porphyrins is about 6.5-6.8 A. Electronic spectra and proton magnetic resonance spectra support the postulated "face-to-face" conformations. A hypothesis that related compounds may serve as multielectron redox catalysts for 02 and N2 is presented. The development of efficient catalysts for the reversible multielectron reduction of 02 and N2 would have great significance. Such catalysts are essential to the oxygen cathode of an air-powered fuel cell and to electrochemical nitrogen fixation.The major problem in catalyzing four-or six-electron reductions of 02 or N2 is that stepwise one-or two-electron paths must pass through relatively unstable intermediates (Fig. 1). The high energy content of these intermediates precludes rapid stepwise electron transfer operating near the reversible potential of the overall four-or six-electron reduction. The rapid reduction of oxygen, which has a triplet ground state, also requires a mechanism to overcome the conservation of spin and orbital angular momentum. The latter problem might be circumvented by using a metal catalyst that has low-lying paramagnetic states. These arguments have been developed by H. Taube (personal communication).Many monometallic macrocyclic complexes adsorbed on graphite have been examined as catalysts for oxygen reduction (3). The most effective macrocycles have four nitrogen donor atoms. In the phthalocyanine series, the order of reactivity is Fe > Co > Ni > Cu > Mn. However, such studies have failed to reveal any catalyst that is capable of reversible reduction of 02 to water, possibly because with a single metal center, initial 2e-reduction to H202 is always dominant.We have approached this problem by constructing a new class of so-called "face-to-face porphyrins" in which two porphyrin rings are held in parallel conformation. Thus, two metal atoms might act in concert to bind and reduce dioxygen (or dinitrogen) is carried out at 250, the measured rates are such that Greenwood and Gibson (4) conclude that any intermediates must have half-lives of less than 10 Msec. Several mono-and dioxygenases, which reduce oxygen with concomitant oxidation of organic substrates, also contain more than one functional metal ion.These include the monooxygenases laccase (mono-phenol monooxygenase, 4 Cu), and ascorbate oxidase (8 Cu) as well as the dioxygenase L-tryptophan oxygenase (2 hemes and 2 Cu).In contrast to the large number of biological systems that reduce 02, evolutionary processes appear to have developed only a single dinitrogen fixing system, nitrogenase (5). Although the molecular mechanism has not yet been elucidated, a binuclear metal site for dinitrogen reduction has been proposed.tAbiological support for the idea of binuclear 02 reduction by Fe2+ comesfrom Hammondand Wu'sstudy (7) ofthe ...

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“…[41][42][43] A representative EPR spectrum of the fenoprofenate-copper complex recorded at room temperature is shown in Figure 1. If the two copper(II) ions are in a moderate interaction, the ground state of the dicupric center is a singlet (S = 0) and the triplet state (S = 1) can be thermally populated.…”

Section: Spectroscopic Characterizations Of [Cu 2 (Fen) 4 (Dmf) 2 ]mentioning

confidence: 99%

Significant anti-inflammatory properties of a copper(II) fenoprofenate complex compared with its parent drug: Physical and chemical characterization of the complex

Agotegaray¹,

Boeris²,

Quinzani³

2010

J. Braz. Chem. Soc.

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A síntese, a caracterização físico-química, as propriedades anti-inflamatórias e a atividade mimética de catecolase do complexo de cobre(II) com a droga anti-inflamatória non-esteroidal Fenoprofeno [ácido 2-(3-fenóxifenil)propiônico] com fórmula [Cu 2 (fen) 2 (dmf) 2 ] (fen = ânion do fenoprofenato, dmf = N,N-dimetilformamida) foram investigadas. Os resultados da análise espectroscópica (espectros de FTIR e EPR) e dados de análise termogravimétrica e térmica diferencial obtidos para o complexo sólido estão de acordo com a sua estrutura dinuclear. Os espectros eletrônicos do produto são igualmente apresentados e discutidos neste trabalho. O complexo foi testado para as suas propriedades anti-inflamatórias em comparação com a droga de referência, o sal de cálcio do Fenoprofeno. A administração oral do composto binuclear inibiu o desenvolvimento do edema induzido por carragenana em ratos; esta inibição foi mais significativa do que a obtida com a droga de referência. O estudo cinético da atividade mimética da catecolase foi realizado espectrofotometricamente, monitorando-se a transformação oxidativa do 3,5-di-terc-butilcatecol na o-quinona correspondente. Os parâmetros cinéticos foram determinados pelo emprego do modelo de Michaelis-Menten, que demonstrou que o novo complexo mimetiza a atividade da catecol oxidase.The synthesis, physicochemical characterization, anti-inflammatory properties and catecholase mimetic activity of the dinuclear complex of copper(II) with the non-steroidal anti-inflammatory drug Fenoprofen [2-(3-phenoxyphenyl)propionic acid] with formula [Cu 2 (fen) 4 (dmf) 2 ] (fen = fenoprofenate anion, dmf = N,N-dimethylformamide) have been investigated. Results of spectroscopic analysis (FTIR and EPR) as well as thermogravimetric and differential thermal analysis data obtained for the solid complex are in good agreement with its dinuclear structure. Electronic spectra of the product are also reported and discussed. The complex was tested for anti-inflammatory properties in comparison to the parent drug, Fenoprofen calcium salt. Oral administration of the dinuclear compound inhibited development of carrageenan-induced oedema in mice; this inhibition was higher than that observed for the parent drug. The kinetic study of the catecholase mimetic activity was carried out spectrophotometrically by monitoring the oxidative transformation of 3,5-di-tert-butylcatechol into the corresponding light-absorbing o-quinone. Kinetic parameters were determined employing the Michaelis-Menten model, showing that the new complex presents catechol oxidase mimetic activity.Keywords: copper(II), Fenoprofen, anti-inflammatory properties, catecholase activity IntroductionThe proposed curative properties of copper(II) carboxylate-based non-steroidal anti-inflammatory drugs (NSAIDs) have led to the development of numerous mononuclear and dinuclear copper(II) complexes of NSAIDs with enhanced anti-inflammatory activity.1,2 The elevation of total blood copper levels during acute as well as chronic inflammatory states has been re...

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The spectral and magnetic properties of copper(II)cyanoacetate

Cited by 146 publications

References 30 publications

Preparation, Infrared Spectra, Electronic Spectra, and Magnetic Moments of Copper(II) Complexes of N-Acetylglycine and Their Amine Adducts

Preparation, Infrared Spectra, Electronic Spectra, and Magnetic Moments of Copper(II) Complexes of N-Acetylglycine and Their Amine Adducts

Synthesis and characterization of "face-to-face" porphyrins.

Significant anti-inflammatory properties of a copper(II) fenoprofenate complex compared with its parent drug: Physical and chemical characterization of the complex

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