Salicylate‐Functionalized Bismuth Oxido Clusters: Hydrolysis Processes and Microbiological Activity

Schlesinger, Maik; Pathak, Amita; Richter, Steffen; Sattler, Dominik; Seifert, Andreas; Rüffer, Tobias; Andrews, Philip C.; Schalley, Christoph A.; Lang, Heinrich; Mehring, M.

doi:10.1002/ejic.201402493

Cited by 20 publications

(18 citation statements)

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“…However, defined intermediates formed during the hydrolysis process of 3 , as reported for Ph 2 Bi(O 3 SR) (R=phenyl, 4‐tolyl), which decompose to BiO(O 3 SR) over ten years and as reported in our previous studies on bismuth silanolates, carboxylates, and nitrates, were not observed. Therefore, [Bi 6 O 4 (OH) 4 (NO 3 ) 6 ]⋅H 2 O ( A ; approach A) and [Bi 38 O 45 (OMc) 24 (dmso) 9 (H 2 O) 2 ]⋅2 DMSO⋅5 H 2 O ( B ; approach B) were used as preorganized starting materials and were treated with 6 and 24 equivalents of vinylsulfonic acid in DMSO, respectively (Scheme ).…”

Section: Resultssupporting

confidence: 56%

“…Therefore, several hydrolysis products of bismuth salicylates, for example, {Bi 4 }, {Bi 9 }, {Bi 22 }, and {Bi 38 } oxido clusters, have been characterized as model compounds to elucidate the composition and structure of poorly defined BSS and to explain the hydrolysis process of bismuth(III) carboxylates. In addition, several bismuth(III) carboxylates, for example, 4‐methylsalicylates and compounds derived from nonsteroidal anti‐inflammatory drugs (NSAID), have been synthesized to study their bactericidal behavior. More recently, bismuth(III) sulfonates have come into focus.…”

Section: Introductionmentioning

confidence: 99%

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Homo‐ and Heteroleptic Coordination Polymers and Oxido Clusters of Bismuth(III) Vinylsulfonates

Wrobel

Rüffer

Korb

et al. 2018

Chemistry A European J

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The synthesis and characterization of six homo- and heteroleptic coordination polymers and oxido clusters of bismuth(III) vinylsulfonates are reported. The solvent-mediated reaction of BiPh and vinylsulfonic acid in ethanol produces [{Ph Bi(O SCH=CH )} ] (1), which crystallizes as a one-dimensional coordination polymer as a result of bridging sulfonato ligands accompanied by intermolecular Bi⋅⋅⋅ π(arene) London dispersion interactions. In solution, compound 1 equilibrates to give [{PhBi(O SCH=CH ) } ] (2) and BiPh . Compound 2 is obtained as a single product by the reaction of BiPh with vinylsulfonic acid in acetonitrile and crystallizes as a one-dimensional coordination polymer. The homoleptic vinylsulfonate [{Bi(O SCH=CH ) } ] (3) was isolated as a two-dimensional coordination polymer, which is quite moisture sensitive, but did not provide a distinct polynuclear bismuth oxido cluster upon hydrolysis. However, by treatment of [Bi O (OH) (NO ) ]⋅H O or [Bi O (OMc) (dmso) (H O) ]⋅2 DMSO⋅5 H O (OMc=methacrylate) with vinylsulfonic acid, such a cluster, namely, [Bi O (OH)(O SCH=CH ) (dmso) ](O SCH=CH )⋅3 DMSO (4), is available as the main product. Starting from the hexanuclear bismuth oxido nitrate, another cluster, [Bi O (NO ) (O SCH=CH ) (dmso) ](O SCH=CH ) ⋅2 DMSO (5), was observed as a co-crystallizing side product, which upon further hydrolysis afforded [Bi O (NO ) (OH) (O SCH=CH ) (dmso) (H O) ](O SCH=CH ) ⋅2 H O (6).

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Section: Resultssupporting

confidence: 56%

Section: Introductionmentioning

confidence: 99%

Homo‐ and Heteroleptic Coordination Polymers and Oxido Clusters of Bismuth(III) Vinylsulfonates

Wrobel

Rüffer

Korb

et al. 2018

Chemistry A European J

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“…No signals were observed in the negative ion ESI-MS, suggesting the formation of bismuth(III) oxido/hydroxido-clusters in solution. 8 22 ], 49 supporting our observations on cluster formation with the unprotected α-amino acid derivatives. † All positive ion ESI-MS spectra showed similar bismuth(III) oxido/hydroxido-clusters fragmentation ions such as [Bi 9 O 7 L 4 (OH) 5 This is not unexpected since in a series of recent papers Mehring and co-workers have used ESI-MS to great effect in identifying and describing the composition of various inorganic and metal-organic bismuth oxido-clusters.…”

Section: Characterisationsupporting

confidence: 61%

Bismuth(iii) complexes derived from α-amino acids: the impact of hydrolysis and oxido-cluster formation on their activity against Helicobacter pylori

et al. 2014

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Eight bismuth(III) complexes derived from a variety of α-amino acids covering a range of physico-chemical properties (L-phenylalanine (Phe), L-proline (Pro), L-methionine (Met), L-cysteine (Cys), D,L-serine (Ser), L-tyrosine (Tyr), l-aspartic acid (Asp) and L-glutamic acid (Glu)) have been synthesised, characterised, and evaluated for their activity against Helicobacter pylori. The optimal synthetic procedure utilises [Bi(O(t)Bu)3], giving the complexes [BiL3] (L = Phe 1, Pro 2, Met 3, Ser 5, Tyr 6) and [Bi2L3] (L = Cys 4, Asp 7, Glu 8) cleanly and in good yield. However, the synthesis is sensitive to both temperature and moisture. The solubility and stability of the bismuth(III) complexes was investigated using ESI-MS. Almost all compounds (except for [Bi(Phe)3] and [Bi(Pro)3]) were found to be partially or completely soluble in aqueous solution giving a pH 2.5-5.0, indicating the presence of free α-amino acid and hydrolysis of the bismuth(III) complexes to polynuclear bismuth oxido-clusters. The results of the bactericidal studies against Helicobacter pylori demonstrate that this hydrolysis process impacts significantly on the observed Minimum Inhibitory Concentration (MICs) which are increased substantially, often by many orders of magnitude, when the complexes are initially prepared in water rather than DMSO.

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“…Among the nuclearities observed for that ligand alone are [ Oxidoclusters supported by alkoxides, other carboxylates and hexafluoroacetylacetonate have also been reported. 7,30,31,[33][34][35][36][37][38][39][40][41][42][43][44][45][46][47] They contain a core composed of Bi(III) and oxygen atoms that has an overall positive charge. These cores are then surrounded by negatively charged carboxylate ligands to form an overall neutral compound.…”

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confidence: 99%

Anionic Bismuth-Oxido Carboxylate Clusters with Transition Metal Countercations

et al. 2016

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Six new anionic bismuth-oxido clusters containing trifluoroacetate ligands were prepared. These include two new BiO clusters: [M(NCMe)(HO)][Bi(μ-O)(μ-OH)(CFCO)] with an octahedral BiO(OH) core (M = Ni, 1a; Co, 1b) and four BiO clusters, {[Co(NCMe)][Bi(μ-O)(CFCO)]} (2a), {[Co{HC(MeCO)(MeCNH)}][Bi(μ-O)(CFCO)]·2[CFCO]·2[CFCOH]·2[HO]} (2b), {[Cu(NCMe)][Bi(μ-O)(CFCO)]·2[CFCOH]} (2c), and {[MeN][Bi(μ-O)(CFCO)]·2[CFCOH]} (2d). These are among the first bismuth-oxido anionic clusters synthesized, and the first to have transition metal countercations. The BiO anion in 1a and 1b is a high-symmetry octahedron. Additionally, two of the new BiO clusters are arranged in 1D polymeric structures via bridging carboxylate ligands. The cation in compound 2c had not been previously characterized and was also observed in the synthesis of [Co{HC(MeCO)(MeCNH)}][Bi(NO)] (3). The new compounds were characterized using single crystal X-ray crystallography and elemental analysis.

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Salicylate‐Functionalized Bismuth Oxido Clusters: Hydrolysis Processes and Microbiological Activity

Cited by 20 publications

References 72 publications

Homo‐ and Heteroleptic Coordination Polymers and Oxido Clusters of Bismuth(III) Vinylsulfonates

Homo‐ and Heteroleptic Coordination Polymers and Oxido Clusters of Bismuth(III) Vinylsulfonates

Bismuth(iii) complexes derived from α-amino acids: the impact of hydrolysis and oxido-cluster formation on their activity against Helicobacter pylori

Anionic Bismuth-Oxido Carboxylate Clusters with Transition Metal Countercations

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