Abstract
Selected rhenium complexes with pyrogallol (1,2,3-trihydroxybenzene) and catechol (1,2-dihydroxybenzene) as strongly bound ligands were prepared by a reaction of rhenium precursor tetrabutylammonium-tetrachlorooxorhenate with twofold molar excess of ligand in presence of various amounts of triethylamine. The structures of formed complexes and their consequent reaction products were estimated by means of mass spectrometry with electrospray ionization. The kinetics of reactions in course of complex formation and consequent decomposition were primarily followed by UV–Vis absorption spectra measurement, complemented by single or continuous electrospray mass spectrometry analyses.
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Abbreviations
- SI:
-
Similarity index
- PG:
-
Pyrogallol
- Cat:
-
Catechol
- Re:
-
Rhenium
- O:
-
Oxygen
- Cl:
-
Chlorine
- Bu:
-
Butyl
- ESI-MS:
-
Mass spectrometry with electrospray ionization
- TEA:
-
Triethylamine
- UV–vis:
-
Ultraviolet–visible absorption spectrometry
- EIC:
-
Extracted ion current
References
Abrams MJ, Murrer BA (1993) Metal compounds in therapy and diagnosis. Science 261:725–730. doi:10.1126/science.8102010
Colton R (1965) The chemistry of rhenium and technetium. Interscience, London
Day EF, Payne TA, Holt CA (2007) Mass spectrometric study of dirhenium biscarboxylate:purine dinucleotide complexes. Rapid Commun Mass Spectrom 21:903–910. doi:10.1002/rcm.2910
Fedorova G, Nebesky V, Randak T, Grabic R (2014) Simultaneous determination of 32 antibiotics in aquaculture products using LC–MS/MS. Chem Pap 68:29–36. doi:10.2478/s11696-013-0428-3
Gerloch M, Constable EG (1994) Transition metal chemistry. VCH Verlagsgesellschaft mbH, Weinheim
Henderson V, Nicholson BK, McCaffrey LJ (1998) Applications of electrospray mass spectrometry in organometallic chemistry. Polyhedron 17:4291–4313. doi:10.1016/S0277-5387(98)00246-0
Hori H, Ishitani O, Koike K, Takeuchi K (1996) Electrospray mass spectrometric detection of unstable rhenium complexes as reaction intermediates of photochemical CO2-fixation. Anal Sci 12:587–590. doi:10.2116/analsci.12.587
Hori H, Ishihara J, Koike K, Takeuchi K, Ibusuki T, Ishitani O (1997) Electrospray mass spectrometric detection of neutral rhenium bipyridine complexes using NaNO3 as an ionization agent. Chem Lett 3:273–274. doi:10.1246/cl.1997.273
Kohlickova M, Jedinakova-Krizova V, Konirova R (1999) Chromatographic study of 186Re complexes with various ligands. J Radioanal Nucl Chem 242:545–549. doi:10.1007/BF02345591
Kohlickova-Koudelkova M, Jedinakova-Krizova V, Deyl Z (2002) Study of perrhenate reduction by capillary electrophoresis. Electrophoresis 23:245–248. doi:10.1002/1522-2683(200202)23:2<245:AID-ELPS245>3.0.CO;2-D
Konirova R, Ernestova M, Jedinakova-Krizova V, Kral V (2003) Radioactive labeled porphyrin derivates. Czech J Phys 53:755–761. doi:10.1007/s10582-003-0098-4
Koudelkova M, Jedinakova-Krizova V (2003) Capillary electrophoretic and thin-layer chromatographic characterization of rhenium complexation with 1-hydroxyethylidenediphosphonic acid. J Chromatogr A 990:317–323. doi:10.1016/S0021-9673(02)01798-3
Kowalczyk L, Szynkowska MI (2012) Oxidation of ammonia using modified TiO2 catalyst and UV–vis irradiation. Chem Pap 66:607–611. doi:10.2478/s11696-012-0159-x
Nicholson T, Kramer DJ, Davison A, Jones AG (2003) The substitution chemistry of a useful new synthon with neutral donor ligands. The reactions of [TcCl3(N = NPh2)(PPh3)2] with phosphine ligands. The X-ray crystal structures of [TcCl2(N = NPh2)(PMe2Ph)3][PF6], [TcCl(N = NPh2)(dppe)2][PF6]2 and [TcCl2(N = NPh2)(TRIPHOS)][BPh4]. Inorg Chim Acta 353:177–182. doi:10.1016/S0020-1693(03)00228-7
Petroselli G, Mandal MK, Chen LC, Ruiz GT, Wolcan E, Hiraoka K, Nonami H, Erra-Balsells R (2012) Mass spectrometry of rhenium complexes: a comparative study by using LDI-MS, MALDI-MS, PESI-MS and ESI-MS. J Mass Spectrom 47:313–321. doi:10.1002/jms.2965
Schrotterova D, Nekovar P (2006) Extraction of Re(VII) by neutral and basic extractants. Chem Pap 60:427–431. doi:10.2478/s11696-006-0078-9
Shaker SA, Khaledi H, Mohd Ali H (2010) Spectroscopic investigations and physic-chemical characterization of newly synthesized mixed-ligand complexes of 2-methylbenzimidazole with metal ions. Chem Pap 65:299–307. doi:10.2478/s11696-011-0003-8
Sticha M, Jelinek I, Polakova J, Kaliba D (2015) Characterization of rhenium(V) complexes with phenols using mass spectrometry with selected soft ionization techniques. Anal Lett 48:2329–2342. doi:10.1080/00032719.2015.1038552
Tisato F, Bolzati C, Porchia M, Refosco F (2004) Contribution of electrospray mass spectrometry for the characterization, design, and development of nitrido technetium and rhenium heterocomplexes as potential radiopharmaceuticals. Spectrom Rev 23:309–332. doi:10.1002/mas.20000
Valliant JF, Riddoch RW, Hughes DW, Roe DG, Farconnier TK, Thornback JR (2001) The solid phase synthesis and NMR spectroscopy of a 99Tc chelate–bombesin derived peptide conjugate. Inorg Chim Acta 325:155–163. doi:10.1016/S0020-1693(01)00637-5
Van Berkel GJ (2003) An overview of some recent developments in ionization methods for mass spectrometry. Eur J Mass Spectrom 9:539–562. doi:10.1255/ejms.586
Wan KX, Vidavsky I, Gross ML (2002) Comparing similar spectra: from similarity index to spectral contrast angle. J Am Soc Mass Spectrom 13:85–88. doi:10.1016/s1044-0305(01)00327-0
Wyatt MF (2011) MALDI–TOFMS analysis of coordination and organometallic complexes: a nic(h)e area to work in. J Mass Spectrom 46:712–719. doi:10.1002/jms.1957
Wyatt MF, Stein BK, Brenton AG (2006) Characterization of various analytes using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and 2-[(2E)-3-(4-tert-butylphenyl)-2-methylprop-2-enylidene]malononitrile matrix. Anal Chem 78:199–206. doi:10.1021/ac050732f
Acknowledgements
This research was carried out within the framework of the project of the Specific University Research (SVV 260317). The Norwegian Financial Mechanism project CZ01116 is gratefully acknowledged.
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Štícha, M., Kaliba, D., Jelínek, I. et al. Analytical study of rhenium complexes with pyrogallol and catechol. Chem. Pap. 71, 819–830 (2017). https://doi.org/10.1007/s11696-016-0088-1
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DOI: https://doi.org/10.1007/s11696-016-0088-1