Kinetics and mechanism of substitution reactions of cobalt(III) trans-dioximines in non-aqueous media

Samus, N. M.; Ablov, A. V.

doi:10.1016/s0010-8545(00)82013-5

Cited by 29 publications

(9 citation statements)

References 27 publications

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“…In contrast to this downward shift, this BF 2 + -bridged complex exhibited an upward shift to about a 1653 cm ±1 . The broad band at 1710 cm ±1 assigned to the O±H´´´O bending vibrations, disappeared upon insertion of the BF 2 groups with the simultaneous appearance of peaks at 1176 and 872 cm ±1 for the B±O and B±F resonances, respectively [4]. The fast atom bombardment mass spectrum of this complex showed a peak at m/z = 1256.4 caused by [M] + and another at m/z = 1177 attributed to the loss of pyridine [M-py] + .…”

Section: Resultsmentioning

confidence: 99%

“…The incorporation of a vicdioxime unit onto the macrocycle provides an efficient binding site for the transition metal cations by the formation of an MN 4 core with additional two hydrogen bridges [3]. The presence of mildly acidic hydroxyl groups and slightly basic nitrogen atoms causes vic-dioximes to be amphoteric ligands which form corrin type square-planar, square-pyramidal and octahedral complexes with transition metal cations such as nickel(II), copper(II), and cobalt(III) as central atoms [4].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of a Novel Macrocyclicvic-Dioxime and Some of its Mono and Trinuclear Complexes

Kanteki̇n

Ocak

Gök

2001

Z. anorg. allg. Chem.

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The (E, E)-dioxime containing a dithia-dioxa-diaza macrocyclic moiety 5,6 : 11,12 : 17,18-tribenzo-2,3-bis(hydroxyimino)-1,4-diaza-7,16-dithia-10,12-dioxacyclooctadecane (H 2 L) has been synthesized in high yield by a 1 + 1 addition of cyanogendi-N-oxide with 2, 3 : 8,9 : 14,15-tribenzo-1,16-diamino-4,13-dithia-7,10-dioxahexadecane (3) which was obtained from condensation reaction with 2-amino thiophenol and 1,2-bis(2-bromoethoxy)benzene, in dichloromethane at ±10°C. Two vic-Dioxime ligands coordinate with Ni(II), Cu(II) and Co(III) through its hydroxyimino nitrogen donor atoms by the loss of the oxime protons. Homo and heterotrinuclear Cu II 3 and Co III Pd II 2 complexes of this ligand have been prepared; their two ligand molecules are connected via hydroxyimino or BF 2 + -bridging groups and two of the metal ions are coordinated by a diaza-dithia mixed donor macrocyclic moiety. The macrocyclic ligand and its transition metal complexes have been characterized on the basis of 1 H-, 13 C-NMR, IR and MS spectroscopy and elemental analysis data. Synthese und Charakterisierung eines neuen vic-Dioxim-Makrocyclus und einiger seiner mono-und trinuklearen MetallkomplexeInhaltsu È bersicht. Das (E,E)-Dioxim mit dem Dithia-dioxodiaza-Makrocyclus 5,6 : 11,12 : 17 : 18-Tribenzo-2,3-bis(hydroxyimino)-1,4-diaza-7,16-dithia-10,12-dioxacyclooctadecan (H 2 L) wurde in hohen Ausbeuten synthetisiert durch 1 + 1 Addition von Dicyan-di-N-oxid mit 2,3 : 8,9 : 14,15-tribenzo-1,16-diamino-4,13-dithia-7,10-dioxahexadecan (3), das durch Kondensationsreaktion von 2-Aminothiophenol und 1,2-Bis(2-bromethoxy)benzol in Dichlormethan bei ±10°C erhalten wurde. Zwei vic-Dioximliganden koordinieren mit Ni II , Cu II bzw. Co III u È ber die Hydroxoimino-Stickstoffatome unter Verlust der Oximprotonen. Homo-und heteronukleare Cu II 3 -und Co III Pd II 2 -Komplexe dieses Liganden wurden dargestellt; ihre beiden Ligandenmoleku È le sind u È ber Hydroxoimino-oder BF 2 + -Bru È cken verbunden und zwei der Metallionen werden durch die N-und S-Donoratome der makrocyclischen Einheit koordiniert. Der makrocyclische Ligand und seine Ûbergangsmetallkomplexe wurden durch 1 H-, 13 C-NMR-, IR-, MS-Spektroskopie sowie durch Elementaranalysen charakterisiert.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of a Novel Macrocyclicvic-Dioxime and Some of its Mono and Trinuclear Complexes

Kanteki̇n

Ocak

Gök

2001

Z. anorg. allg. Chem.

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“…Nevertheless, there is one particular class of low molecular weight organic compounds that can act as ligands for binding silver(I) cations and will form complexes that satisfy the specific requirements outlined above. These compounds are oximes, which represent versatile organic molecules that were extensively used as excellent ligands in analytical [15], inorganic [16-20] and bioinorganic chemistry [21-23]. Cyanoximes – compounds with the general formula HON=C(CN)-R (R = electron withdrawing group) – represent a new, special class of biologically active molecules [24], and their chemistry and biomedical applications have been intensively developed in the last two decades [25].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of two cyanoxime ligands, their precursors, and light insensitive antimicrobial silver(I) cyanoximates

Riddles

Whited

Lotlikar

et al. 2014

Inorganica Chimica Acta

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High-yield syntheses of N-piperidine-cyanacetamide (1), N-morpholyl-cyanacetamide (4) and their oxime derivatives N-piperidine-2-cyano-2-oximino-acetamide (HPiPCO, 2) and N-morpholyc-2-cyano-2-oximino-acetamide (HMCO, 5) were developed using two-step preparations. At first, the reactions of neat cyanoacetic acid esters and the respective cyclic secondary amines such as piperideine and morpholine afforded pure cyanacetamides, which were converted into cyanoximes at room temperature using the nitrosation reaction with gaseous CH3ONO. The synthesized compounds were investigated by means of IR, 1H, 13C and UV-visible spectroscopy. Crystal structures of two starting substituted cyan-acetamides and two target cyanoximes were determined. Silver(I) complexes of AgL composition (L = PipCO, 3; MCO, 6) were prepared in high yield. Both metal complexes are thermally stable above 100oC, and remarkably stable to high intensity visible light. The stability of dried AgL compounds towards short wavelength UV-radiation (a frequently used germicidal light) was examined using diffusion reflectance spectroscopy. Both complexes demonstrate slow photoreduction within ~3 hrs, observable as a gradual color change and darkening due to the formation of fine (nano-scale) particles of metallic silver. The complex Ag(MCO), 6, is about 2.6 times less stable towards UV-radiation than its more lypophyllic analog Ag(PipCO), 3. Antimicrobial and biofilm growth inhibition properties of the prepared solid acrylate-based polymeric composites containing embedded silver(I) cyanoximates were investigated using three human pathogens: P. aeruginosa PAO1 (wound isolate), S. aureus NRS70 (methicillin resistant respiratory isolate), and S. mutans UA159 (cariogenic dental isolate). Studies showed that both 3 and 6 compounds completely abolished the growth of PAO1 at 0.5 weight % concentration, and the growth of UA159 and NRS70 at 1% concentration. Moreover, data demonstrates that complexes 3 and 6 also inhibit both planktonic and biofilm growth of Gram-positive and Gram-negative bacterial pathogens. The demonstrated thermal stability and pronounced antimicrobial activity of both silver(I) cyanoximates indicates the strong potential for the studied complexes to be used as light insensitive antimicrobial additives to light-curable adhesives that set indwelling devices in place.

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“…The incorporation of vic-dioxime unit onto the macrocycle provides an efficient binding site for the transition metal cations by the formation of an MN 4 core with additional two hydrogen bridges (5-7). The presences of mildly acidic hydroxyl groups and slightly basic nitrogen atoms causes vic-dioximes to be amphoteric ligands which forms corrin type square-planar, square-pyramidal and octahedral complexes with transition metal cations such as Ni(II), Cu(II) and Co(II) as central atoms (8)(9)(10)(11). Synthetic macrocycles have been known for over 75 years, although a real spate of publications in this area occurred in the late 1960's (12,13).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of a New Dioxime and Its Heterotrinuclear BF₂⁺Capped Complexes

Uysal

Coşkun

Koç

et al. 2008

Journal of Macromolecular Science, Part A

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v-Isonitrosoacetophenone (1), phenylglyoxime (2), chlorophenylglyoxime (1), dopaminophenylglyoxime (3) and [(salen/saloph)Fe] 2 O (4) have been synthesized as described in the literature procedure. [Fe(III)(salen/saloph)dopaminophenylglyoxime)] (starting complexes) have been synthesized from dopaminophenylglyoxime and tetradentate schiff bases which contain dinuclear Fe(III) oxygen-bridges N,N 0 -bis(salicylidene)ethylenediamine (salenH 2 ) and bis(salicylidene)-o-phenylenediamine (salophH 2 ). The new heterotrinuclear complexes have been obtained from starting complexes and Co(II), Ni(II), Cu(II) salts. Then, heterotrinuclear vic-dioxime complexes containing BF 2 þ capped have been synthesized. The complexes have been characterized as low-spin distorted octahedral Fe(III) bridged by o-hydroxyphenolic groups. The o-hydroxyphenolic groups play a role as bridges for weak antiferromagnetic intramolecular exchange. The structure of dioxime and its complexes were identified by using elemental analysis, ICP-AES, 1 H-NMR and IR spectral data.

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Kinetics and mechanism of substitution reactions of cobalt(III) trans-dioximines in non-aqueous media

Cited by 29 publications

References 27 publications

Synthesis and Characterization of a Novel Macrocyclicvic-Dioxime and Some of its Mono and Trinuclear Complexes

Synthesis and Characterization of a Novel Macrocyclicvic-Dioxime and Some of its Mono and Trinuclear Complexes

Synthesis and characterization of two cyanoxime ligands, their precursors, and light insensitive antimicrobial silver(I) cyanoximates

Synthesis and Characterization of a New Dioxime and Its Heterotrinuclear BF₂⁺Capped Complexes

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Kinetics and mechanism of substitution reactions of cobalt(III) trans-dioximines in non-aqueous media

Cited by 29 publications

References 27 publications

Synthesis and Characterization of a Novel Macrocyclicvic-Dioxime and Some of its Mono and Trinuclear Complexes

Synthesis and Characterization of a Novel Macrocyclicvic-Dioxime and Some of its Mono and Trinuclear Complexes

Synthesis and characterization of two cyanoxime ligands, their precursors, and light insensitive antimicrobial silver(I) cyanoximates

Synthesis and Characterization of a New Dioxime and Its Heterotrinuclear BF2+Capped Complexes

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Synthesis and Characterization of a New Dioxime and Its Heterotrinuclear BF₂⁺Capped Complexes