Electrospray ionization mass spectrometric investigations of the complexation behavior of macrocyclic thiacrown ethers with bivalent transitional metals (Cu, Co, Ni and Zn)

Rapid Communications in Mass Spectrometry

Volumn 26, Issue 19, 2012, Pages 2287-2294

  Tsybizova, Alexandra ^a   Tarábek, Ján ^a   Buchta, Michal ^a   Holaý, Petr ^a   Schröder, Detlef ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPOUNDS; CROWN ETHERS; ELECTRODEPOSITION; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTROSPRAY IONIZATION; ETHERS; HEAVY METALS; LIGANDS; MASS SPECTROMETERS; MASS SPECTROMETRY; NICKEL; PARAMAGNETIC RESONANCE;

% REDUCTIONS; 3D METALS; BINDING CONSTANT; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; MACROCYCLICS; METALS IONS; SELECTIVE EXTRACTION; THIACROWN; THIACROWN ETHERS; TRANSITIONAL METALS;

METAL IONS;

EID: 84866057473     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.6352     Document Type: Article

References (49)

1. J. P. Vernet,. Heavy Metals in the Environment. Elsevier, New York, 1991.
2. C. Gros, F. Rabiet, F. Denat, S. Brandes, H. Chollet, R. Guilard,. New silica-gel-bound polyazacycloalkanes and characterization of their copper(II) complexes using electron spin resonance spectroscopy. J. Chem. Soc., Dalton Trans. 1996, 7, 1209.
3. H. Chollet, J. L. Babouhot, F. Barbette, R. Guilard,. Chelating cation-exchange resins containing grafted polyazacycloalkanes for removal of metals from wastewater. PCT Int. Appl. WO 2001015806, 2001.
4. B. Vaidya, M. D. Porter, M. D. Utterback, R. A. Bartsch,. Selective determination of cadmium in water using a chromogenic crown ether in a mixed micellar solution. Anal. Chem. 1997, 69, 2688.
5. E. E. Laney, J. H. Lee, J. S. Kim, X. Huang, Y. Jang, H. S. Hwang, T. Hayashita, R. A. Bartsch,. Sorption of lead(II) by proton-ionizable polyether resins. React. Funct. Polym. 1998, 36, 125.
6. II extraction studies of a novel thiacrown polymer. Chem. Commun. 1998, 1637.
7. A. J. Nelson, J. G. Reynolds, T. F. Baumann, G. A. Fox,. X-ray photoemission investigation of binding sites in polymer-bound thiacrowns used for environmental remediation of Hg in aqueous solutions. Appl. Surf. Sci. 2000, 167, 205.
8. 5). React. Funct. Polym. 2000, 44, 111.
9. W. Sim, J. Y. Lee, J. Kwon, M. J. Kim, J. S. Kim,. Novel 1,3-alternate calix[4]thiacrown ethers. Bull. Korean Chem. Soc. 2002, 23, 879.
10. K. Yamashita, K. Kurita, K. Ohara, K. Tamura, M. Nango, K. Tsuda,. Syntheses of thiacrown ethers polymers and their application for heavy metal ion adsorbents. React. Funct. Polym. 1996, 31, 47.
11. B. Saad, S. M. Sultan,. Extraction spectrophotometric determination of mercury(II) using thiacrown ethers and Bromocresol Green. Talanta 1995, 42, 1349.
12. A. T. Yordanov, D. M. Roundhill,. Chemically modified calix[4]arenes as selective complexants for heavy metal ions: Comparison with crowns and thiacrowns. New J. Chem. 1996, 20, 447.
13. S. M. Williams, J. S. Brodbelt, A. P. Marchand, D. Cal, K. Mlinaric-Majerski,. Metal complexation of thiacrown ether macrocycles by electrospray ionization mass spectrometry. Anal. Chem. 2002, 74, 4423.
14. C. J. Pedersen,. Macrocyclic polyether sulfides. J. Org. Chem. 1971, 36, 254.
15. S. G. Murray, F. R. Hartley,. Coordination chemistry of thioethers, selenoethers, and telluroethers in transition-metal complexes. Chem. Rev. 1981, 81, 365.
16. H. K. Frensdorff,. Stability constants of cyclic polyether complexes with univalent cations. J. Am. Chem. Soc. 1971, 93, 600.
17. N. S. Poonia,. Coordination chemistry of sodium and potassium complexation with macrocyclic polyethers. J. Am. Chem. Soc. 1974, 96, 1012.
18. R. M. Izatt, J. S. Bradshaw, S. A. Nielsen, J. D. Lamb, J. J. Christensen,. Thermodynamic and kinetic data for cation-macrocycle interaction. Chem. Rev. 1985, 85, 271.
19. L. J. Rodriguez, M. Xu, E. M. Eyring, S. Petrucci,. Molecular dynamics of macrocycle-metal ion complexes involving heteronuclear binding atoms. Pure Appl. Chem. 1989, 61, 1593.
20. Z. Zong, S. Dong, Y. Hu, Y. Xu, W. Liu,. Synthesis and complexation properties of polystyrene supported polymeric thiacrown ether. Eur. Polym. J. 1998, 34, 761.
21. M. Yamashita, J. B. Fenn,. Electrospray ion source. Another variation on the free-jet theme. J. Phys. Chem. 1984, 88, 4451.
22. J. B. Fenn, M. Mann, C. K. Meng, S. F. Wong, C. M. Whitehouse,. Electrospray ionization-principles and practice. Mass Spectrom. Rev. 1990, 9, 37.
23. R. D. Smith, J. A. Loo, C. G. Edmonds, C. J. Barinaga, H. R. Udseth,. New developments in biochemical mass spectrometry: electrospray ionization. Anal. Chem. 1990, 62, 882.
24. R. B. Cole,. Electrospray Ionization Mass Spectrometry. Wiley-Interscience, New York, 1997.
25. P. Kebarle,. A brief overview of the present status of the mechanisms involved in electrospray mass spectrometry. J. Mass Spectrom. 2000, 35, 804.
26. S. M. Blair, E. C. Kempen, J. S. Brodbelt,. Determination of binding selectivities in host-guest complexation by electrospray/quadrupole ion trap mass spectrometry. J. Am. Soc. Mass Spectrom. 1998, 9, 1049.
27. V. B. Di Marco, G. G. Bombi,. Electrospray mass spectrometry (ESI-MS) in the study of metal-ligand solution equilibria. Mass Spectrom. Rev. 2006, 25, 347.
28. D. Schröder,. Ion clustering in electrospray mass spectrometry of brine and other electrolyte solutions. Phys. Chem. Chem. Phys. 2012, 14, 6382.
29. I. Starke, S. Fürstenberg, H. Müller, H. J. Holdt, E. Kleinpeter,. Electrospray mass spectrometric studies of the complexational behavior of maleonitrile thiacrown ethers with various metals. Rapid Commun. Mass Spectrom. 2006, 20, 897.
30. P. Holý, M. Buchta, J. Rybáček, J. Hodačová, I. Císařová,. Synthesis of electron-rich thiamacrocycles. Synthesis 2010, 4169.
31. A. Tintaru, J. Roithová, D. Schröder, L. Charles, I. Jušinski, Z. Glasovac, M. Eckert-Maksić,. Generation and dissociation pathways of singly and doubly protonated bisguanidines in the gas phase. J. Phys. Chem. A 2008, 112, 12097.
32. R. A. J. O'Hair,. The 3D quadrupole ion trap mass spectrometer as a complete chemical laboratory for fundamental gas-phase studies of metal mediated chemistry. Chem. Commun. 2006, 1469.
33. +. J. Mass Spectrom. 2010, 45, 1246.
34. E. L. Zins, C. Pepe, D. Schröder,. Energy-dependent dissociation of benzylpyridinium ions in an ion-trap mass spectrometer. J. Mass Spectrom. 2010, 45, 1253.
35. N. G. Tsierkezos, M. Buchta, P. Holý, D. Schröder,. Complexation of late transition metal(II) ions (M = Co, Ni, Cu, and Zn) by a macrocyclic thiacrown ether studied by means of electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 2009, 23, 1550.
36. L. Ginanelli, V. Amendola, L. Fabbrizzi, P. Pallavicini, G. G. Mellerio,. Investigation of reduction of Cu(II) complexes in positive-ion mode electrospray mass spectrometry. Rapid Commun. Mass Spectrom. 2001, 15, 2347.
37. + complexes generated by electrospray ionization. Int. J. Mass Spectrom. 2002, 219, 729.
38. H. Lavanant, H. Virelizier, Y. Hoppilliard,. Reduction of copper(II) complexes by electron capture in an electrospray ionization source. J. Am. Soc. Mass Spectrom. 1998, 9, 1217.
39. A. Tintaru, L. Charles, P. Milko, J. Roithová, D. Schröder,. Redox reactions of copper(II) upon electrospray ionization in the presence of acridine ligands with an amide side chain. J. Phys. Org. Chem. 2009, 22, 229.
40. S. Colette, B. Amekraz, C. Madic, L. Berthon, G. Cote, C. Moulin,. Use of electrospray mass spectrometry (ESI-MS) for the study of europium(III) complexation with bis(dialkyltriazinyl)pyridines and its implications in the design of new extracting agents. Inorg. Chem. 2002, 41, 7031.
41. S. Colette, B. Amekraz, C. Madic, L. Berthon, G. Cote, C. Moulin,. Trivalent lanthanide interactions with a terdentate bis(dialkyltriazinyl) pyridine ligand studied by electrospray ionization mass spectrometry. Inorg. Chem. 2003, 42, 2215.
42. Á. Révész, D. Schröder, J. Svec, M. Wimmerová, V. Šindeláař,. Anion binding by bambus[6]uril probed in the gas phase and in solution. J. Phys. Chem. A 2011, 115, 11378.
43. E. C. Kempen, J. S. Brodbelt,. A method for the determination of binding constants by electrospray ionization mass spectrometry. Anal. Chem. 2000, 72, 5411.
44. F. Arnaud-Neu, R. Delgado, S. Chaves,. Critical evaluation of stability constants and thermodynamic functions of metal complexes of crown ethers. Pure Appl. Chem. 2003, 75, 71.
45. P. Milko, J. Roithová, D. Schröder, J. Lemaire, H. Schwarz, M. C. Holthausen,. The phenolato copper(II)/phenol cation as a minimalistic model of the active centers in some copper-containing enzymes. Chem. Eur. J. 2008, 14, 4318.
46. L. Ducháčková, J. Roithová, P. Milko, J. Žabka, N. Tsierkezos, D. Schröder,. Comparative Study of mono- and dinuclear complexes of late 3d-metal chlorides with N,N-dimethylformamide in the gas phase. Inorg. Chem. 2011, 50, 771.
47. J. Jaklová Dytrtová, M. Jakl, D. Schröder, E. Čadková, M. Komárek,. Complexation between the fungicide tebuconazole and copper(II) probed by electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 2011, 25, 1037.
48. E. C. Constable, S. Decurtins, C. E. Housecroft, T. D. Keene, C. G. Palivan, J. R. Price, J. A. Zampese,. Half a grid is better than no grid: competition between 2,2':6',2''-terpyridine and 3,6-di(pyrid-2-yl)pyridazine for copper(II). Dalton. Trans. 2010, 39, 2337.
49. F. Gerson, W. Huber,. Electron Spin Resonance Spectroscopy of Organic Radicals. Wiley-VCH, Weinheim, 2003.