Synthesis and Characterisation of Novel (Guanidine)manganese Complexes and Their Application in the Epoxidation of 1‐Octene

Wortmann, Ramona; Flörke, Ülrich; Sarkar, Biprajit; Umamaheshwari, Venkatesan; Gescheidt, Georg; Herres‐Pawlis, Sonja; Henkel, Gerald

doi:10.1002/ejic.201000836

Cited by 22 publications

(10 citation statements)

References 62 publications

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“…The trinuclear linear compound [Mn 3 (2,2′-bipy) 2 (C 3 H 3 O 2 ) 6 ] is framed in structural prototype presented in literature [Mn 3 (RCOO) 6 (N–N) 2 ], where:RCOO − is the anion of isobutyrate and N–N is 1,10-phenantroline/2,2′-bipyridine [32];RCOO − is the acetate ion, while N–N is 2,2′-bipyridine [33], 1,10-phenantroline [34], 2,2′-bis(1-methylimidazolyl)-phenylmetoxymethane [35], 2-(2-pyridyl)benzimidazole [36], N -(1,3-dimethylimidazolidin-2-ylidene)quinolin-8-amine [37];RCOO − is chloroacetate and N–N is 2,2′-bipyridine [38]. …”

Section: Resultsmentioning

confidence: 99%

“…RCOO − is the acetate ion, while N–N is 2,2′-bipyridine [33], 1,10-phenantroline [34], 2,2′-bis(1-methylimidazolyl)-phenylmetoxymethane [35], 2-(2-pyridyl)benzimidazole [36], N -(1,3-dimethylimidazolidin-2-ylidene)quinolin-8-amine [37];…”

Section: Resultsmentioning

confidence: 99%

“…This coordination behavior of carboxylate ligands is encountered mainly in trinuclear linear complexes similar to this one [32,37,38,39,41]. …”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Structural Characterization, Antimicrobial Activity, and In Vitro Biocompatibility of New Unsaturated Carboxylate Complexes with 2,2′-Bipyridine

Scăeţeanu

Chifiriuc

Bleoţu³

et al. 2018

Molecules

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The synthesis, structural characterization, cytotoxicity, and antimicrobial properties of four new complexes formed by employing acrylate anion and 2,2′-bipyridine are reported herein. X-ray crystallography revealed the trinuclear nature of [Mn3(2,2′-bipy)2(C3H3O2)6] (1), meanwhile complexes with general formula [M(2,2′-bipy)(C3H3O2)2(H2O)x]∙yH2O ((2) M: Ni, x = 1, y = 0; (3) M: Cu, x = 1, y = 0; (4) M: Zn, x = 0, y = 1; 2,2′-bipy: 2,2′-bipyridine; C3H3O2: acrylate anion) were shown to be mononuclear. The lowest minimum inhibitory concentration (MIC) of 128 μg mL−1 was recorded for all four tested complexes against Candida albicans, for complex (3) against Escherichia coli, and for complex (4) against Staphylocococcus aureus. Compounds (3) and (4) were also potent efflux pumps activity inhibitors (EPI), proving their potential for use in synergistic combinations with antibiotics. Complexes (1)–(4) revealed that they were not cytotoxic to HCT-8 cells. They also proved to interfere with the cellular cycle of tumour HCT-8 cells by increasing the number of cells found in the S and G2/M phases. Taken together, these results demonstrate the potential of zinc and copper complexes for use in the development of novel antimicrobial and anti-proliferative agents.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthesis, Structural Characterization, Antimicrobial Activity, and In Vitro Biocompatibility of New Unsaturated Carboxylate Complexes with 2,2′-Bipyridine

Scăeţeanu

Chifiriuc

Bleoţu³

et al. 2018

Molecules

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“…The complexes with metals in oxidation state +II attain relatively high ρ-values of 0.98-1.00. The manganese complexes have been shown to be active catalysts for the epoxidation of 1-octene with peracetic acid [74]. The zinc complexes are highly active lactide polymerisation catalysis and are summarised in Sect.…”

Section: Hybridguanidinesmentioning

confidence: 99%

Guanidine Metal Complexes for Bioinorganic Chemistry and Polymerisation Catalysis

Stanek

Rösener

Metz

et al. 2015

Topics in Heterocyclic Chemistry

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Guanidines are highly useful ligands which have conquered coordination chemistry within the last 20 years. Their CN 3 moiety allows multiple substitution patterns which enables tailoring them to a large variety of applications, ranging from bioinorganic coordination chemistry via medicinal chemistry to polymerisation catalysis. In bioinorganic chemistry, guanidines gave important stimuli in the modelling of copper type 1, 2 and 3 enzymes. This review provides with a comprehensive overview on complexes which have been reported with neutral guanidine ligands. Peralkylated guanidines as well as bicyclic or more complex guanidine-comprising entities are described in their coordination chemistry with transition and main-group metals. The structural features of the complexes as well as their most prominent features in bioinorganic chemistry or polymerisation catalysis are highlighted. Hereby, the role of the delocalisation of the positive charge within the guanidine unit gained during coordination is discussed in its importance for efficient and robust coordination. The delocalisation within the CN 3 unit can be measured by the structural value ρ which is discussed for numerous systems. The charge delocalisation makes neutral guanidines versatile and efficient for the stabilisation of highly different coordination modes and a large variety of oxidation states.

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“…[1][2][3][4][5][6] A number of zinc complexes with guanidine or guanidinate ligands have been synthesized and applied as catalysts for the polymerization of lactide [7][8][9][10][11][12][13] and epoxidation of olefins. [14] Bicyclic, monoanionic guanidinate ligands, formed by the deprotonation of neutral guanidines, such as hppH (1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine), Htbn (1,5,7-triazabicyclo[4. 3.0]non-6-ene) and Htbo (1,4,6-triazabicyclo [3.3.0]-oct-4-ene) (Scheme 1), were applied to the synthesis of dinuclear transition metal complexes with multiple bonding between the metals, [15][16][17] catalytically active complexes or dinuclear main group element compounds of special reactivity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Oligomeric Zinc Complexes with Bicyclic and Acyclic Guanidinate Ligands

et al. 2012

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Keywords: Zinc / Oligomeric complexes / Alkyl complexes / N ligands / Hydrogen bonds / GuanidinesZinc dichloride and dimethylzinc were treated with several acyclic and bicyclic guanidines. Three different bicyclic guanidines and their potassium guanidinate salts were treated with ZnCl 2 . The reaction with the neutral guanidines afforded mononuclear complexes, stabilized by intramolecular hydrogen bonding. The reaction with the potassium guanidinate salts led to trinuclear complexes, which were extremely water sensitive. The reaction in the presence of added water furnished a tetranuclear complex with a central OZn 4 unit in good yield, to which six guanidinate ligands were bound.

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Synthesis and Characterisation of Novel (Guanidine)manganese Complexes and Their Application in the Epoxidation of 1‐Octene

Abstract: The synthesis of manganese complexes of the guanidinepyridine hybrid ligands DMEGqu (L1) and TMGqu (L2)

Cited by 22 publications

References 62 publications

Synthesis, Structural Characterization, Antimicrobial Activity, and In Vitro Biocompatibility of New Unsaturated Carboxylate Complexes with 2,2′-Bipyridine

Synthesis, Structural Characterization, Antimicrobial Activity, and In Vitro Biocompatibility of New Unsaturated Carboxylate Complexes with 2,2′-Bipyridine

Guanidine Metal Complexes for Bioinorganic Chemistry and Polymerisation Catalysis

Synthesis of Oligomeric Zinc Complexes with Bicyclic and Acyclic Guanidinate Ligands

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