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1
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Binuclear copper complexes with non-steroidal anti-inflammatory drugs as studied by electrospray ionization mass spectrometry

100%
Kowcun K., Frańska M., Frański R.
Open Chemistry
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2012
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vol. 10
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issue 2
320-326
EN
The solutions containing one of the copper salts (CuCl2, Cu(ClO4)2, Cu(NO3)2, and CuSO4) and one of the non-steroidal anti-inflammatory drugs (NSAIDs, ibuprofen, ketoprofen or naproxen) were analyzed by electrospray ionization mass spectrometry. Three of the salts, namely CuCl2, Cu(ClO4)2 and Cu(NO3)2, yielded binuclear complexes of drug:metal stoichiometry 1:2. Existence of the complexes of such stoichiometry has not been earlier observed. For copper(II) chloride the complexes (ions of the type [M-HCOOH+Cu2Cl]+ and [M+Cu2Cl]+, M stands for the drug molecule) were formed in the gas phase. When copper(II) perchlorate or copper(II) nitrate was used, the observed binuclear copper complexes (ions of the type [M-H+Cu2(ClO4)2+CH3OH]+, [M-H+Cu2(ClO4)2]+ and [M-H+Cu2(NO3)2+CH3OH]+, [M-H+Cu2(NO3)2]+) were observed at low cone voltage, thus these complexes must have already existed in the solution analysed. Therefore, such complexes may also exist under physiological conditions. [...]
2
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Phenylcopper(I) clusters in the gas phase obtained by laser desorption/ionization from bis(dibenzoylmethane)copper(II)

100%
Frański R., Kozik T., Staniszewski B., Urbaniak W.
Open Chemistry
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2010
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vol. 8
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issue 3
508-512
EN
It has been demonstrated that phenylcopper(I)-containing clusters are generated in the gas phase from bis(dibenzoylmethane) copper(II) (Cu(dbm)2) by laser desorption/ ionization (LDI) method. For example, the [Cu5dbm2(C6H5)2]+ ion can be considered as consisting of two Cudbm molecules, two CuC6H5 molecules and a Cu+ cation. The [Cu5(C6H5)4]+ ion can be considered as phenylcopper(I) cluster (consisting of four phenylcopper molecules) ionized by additional Cu+ cation. Results from MS/MS (tandem mass spectrometry) experiments have confirmed the presence of phenylcopper molecules in the analyzed clusters. Ease of preparation of dibenzoylmethane-metal complexes and straightforward method to obtain LDI mass spectra offer a wide range of possibilities to study similar organometallic clusters in the gas phase. [...]
3
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Application of mass spectrometry to structural identification of flavonoid monoglycosides isolated from shoot of lupin (Lupinus luteus L.)

88%
Frański R., Bednarek P., Siatkowska D., Wojtaszek P., Stobiecki M.
Acta Biochimica Polonica
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1999
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vol. 46
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issue 2
459-473
4
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Copper complexes formed by 3,5-bis(2,2′-bipyridin-4-ylethynyl)benzoic acid and its methyl and ethyl esters as studied by electrospray ionization mass spectrometry

76%
Frański R., Kowalska M., Czerniel J., Zalas M., Gierczyk B., Cegłowski M., Schroeder G.
Open Chemistry
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2013
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vol. 11
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issue 12
2066-2075
EN
Electrospray ionization mass spectrometry was used to study the complexes of ligands containing two bipyridine units, namely 3,5-bis(2,2-bipyridin-4-ylethynyl)benzoic acid (1) and its methyl and ethyl esters (2, 3), with copper cation, with CuCl2 as a source of copper. It was found that the type of complexes formed strongly depends on CuCl2 concentration. At lower CuCl2 concentration, the detected complexes were rather simple and some of them were formed upon electrospray ionization conditions e.g. ions [22+Cu2]2+ and [32+Cu2]2+ (complexes ligand-Cu(I) of stoichiometry 2:2) which are analogical to the well known, for quaterpyridine, helical complexes. At higher CuCl2 concentration, the detected complexes were more complicated, and most of them contained copper cations bridged by chlorides. The largest ions were [L2+Cu4Cl6]2+. The CID MS/MS spectra of these ions allowed determination of their mass spectrometric fragmentation pathways and as a consequence their structure elucidation. [...]
5
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Unexpected formation of [M]2+from [M+CuCl+H]2+ions under CID conditions, where M is a molecule of 3,5-bis(2,2’-bipyridin-4-ylethynyl)benzoic acid or its methyl ester

76%
Frański R., Zalas M., Gierczyk B., Cegłowski M., Schroeder G., Kozik T., Hoffmann M.
Open Chemistry
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2015
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vol. 13
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issue 1
EN
[M+CuCl+H]2+ ions were generated using electrospray ionization (ESI); where M is a molecule of 3,5-bis(2,2’-bipyridin-4-ylethynyl)benzoic acid or its methyl ester (1 and 2, respectively). The ions were subjected to CID-MS/MS analysis. It was found that their gas phase decomposition lead to the formation of rare di-cations [M]2+, namely [1]2+ and [2]2+ ions. The formation of [1]2+ ion from [3+H+CuCl]2+ ion in the second fragmentation, where 3 is ethyl ester of 3,5-bis(2,2-bipyridin-4-ylethynyl)benzoic acid, was also observed since in the first fragmentation step the loss of ethylene molecule from [3+H+CuCl]2+ ion took place. To the best of our knowledge, it is the first time that [M]2+ ions formation from respective metal complexes has been reported. It is also unusual that formation of [M]2+ ions is not accompanied by formation of [M]+∙ ions. Furthermore, as expected, theoretical calculation and electron ionization mass spectra show that 1 and 2 are not especially prone to form [M]2+ ions. Thus formation of [M]2+ ions under CID conditions is very surprising.
6
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Electrospray ionization mass spectrometric study of mercury complexes of N-heterocyclic carbenes derived from 1,2,4-triazolium salt precursors

76%
Frański R., Gierczyk B., Schroeder G., Pieper S., Springer A., Linscheid M.
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EN
By mixing 1,2,4-triazolium salts (precursors of N-heterocyclic carbenes 1–6) with mercury acetate, a number of complexes have been obtained under electrospray ionization condition. Carbenes 1 and 2 contain one carbene center; therefore, they are able to bond only one mercury cation. Carbenes 3–5 contain two carbene centers; therefore, they can bond two mercury cations. Mercury complexes of 1–5 always contain an acetate anion attached to a mercury cation. Carbene 6 also contains two carbene centers; however, its structure allows formation of a complex containing mercury bonded simultaneously to both centers, therefore, the complex that does not contain an acetate anion. The MS/MS spectra taken for complexes of carbenes 1–5 have shown formation of a cation corresponding to N1 substituent (adamantyl or benzyl), and those of complexes of carbenes 3–5 (doubly charged ions) have also shown the respective complementary partner ions. Mercury complex of 2 has yielded some other interesting fragmentation pathways, e.g. a loss of the HHgOOCCH3 molecule. The fragmentation pathway of the mercury complexes of 6 was found to be complicated.
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