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2006 | 4 | 2 | 351-362
Tytuł artykułu

Bifunctional sulfur-silicon podands as new nucleophilic ionophores in acyl transfer reactions. Influence of monovalent cations on the reaction kinetics

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Two bifunctional sulfur-silicon nucleophilic ionophores 3-(trimethoxysilyl)-propanethiol (Nu1) and 3-(tri-2-methoxyethoxysilyl)-propanethiol (Nu2) were used as reagents in the acyl transfer reaction studied by kinetic methods. Nuclear magnetic resonance (NMR) and electro-spray ionisation mass spectrometry (ESI MS) were used for determination of the stoichiometry and stability constants of the complexes made by the podands and lithium or sodium ions in acetonitrile solution.
Wydawca

Czasopismo
Rocznik
Tom
4
Numer
2
Strony
351-362
Opis fizyczny
Daty
wydano
2006-06-01
online
2006-06-01
Twórcy
  • Faculty of Chemistry, A. Mickiewicz University, 60-780, Poznań, Poland
  • Faculty of Chemistry, A. Mickiewicz University, 60-780, Poznań, Poland
  • Institute of Physical Organic and Coal Chemistry, NAS, 340114, Donetsk, Ukraine
Bibliografia
  • [1] B. Brzezinski, B. Różalski, G. Schroeder, F. Bartl and G. Zundel: “Excess proton hydrate structures with large proton polarizability in the channel of trioxaalkyl phosphate”, J. Chem. Soc., Farad. T, Vol. 94, (1998), pp. 2093–2096. [Crossref]
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  • [4] B. Łęska, I. Kałużna, B. Gierczyk, G. Schroeder, P. Przybylski and B. Brzezinski: “Kinetic studies of complexation reaction of polyoxaalkyl phosphates with Fe (III) in ethanol”, J. Mol. Struct., Vol. 643, (2002), pp. 9–19.
  • [5] B. Gierczyk, B. Łęska, B. Brzezinski and G. Schroeder: “Podand solvents for organic reactions”, Supramol. Chem., Vol. 14, (2002), pp. 497–502. http://dx.doi.org/10.1080/1061027021000039742[Crossref]
  • [6] A. Maia, D. Landini, B. Łęska and G. Schroeder: “Silicon polypodands: powerful metal cation complexing agents and solid-liquid phase-transfer catalysts of new generation”, Tetrahedron Lett., Vol. 44, (2003), pp. 4149–4151 http://dx.doi.org/10.1016/S0040-4039(03)00838-4[Crossref]
  • [7] B. Łęska, B. Gierczyk, K. Eitner, V.I. Rybachenko and G. Schroeder: “Studies of silicon podand solvents”, Supramol. Chem., Vol. 16, (2004), pp. 303–310.
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  • [9] A. Maia, D. Landini, C. Betti, B. Łęska and G. Schroeder: “Catalytic activity and anion activation in SN2 reactions promoted by complexes of silicon polypodands. Comparision with traditional polyethers”, New J. Chem., Vol. 29, (2005), pp. 1195–1198. http://dx.doi.org/10.1039/b504980f[Crossref]
  • [10] B. LŁeska, G. Schroeder, T. Łuczak, P. Przybylski, R. Pankiewicz, M. Bełtowska-Brzezinska and B. Brzezinski: “Structure and electrochemical reactivity of 3-mercaptopropyl-tris-(3-oxabutoxy)-silane adsorbed on silver surface”, Thin Solid State, in press
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  • [18] V.I. Rybachenko, G. Schroeder, K.Yu. Chotii, V.V. Kovalenko, B. Łęska and A.N. Redko: “Rate and equilibrium of acetyl exchange reactions between pyridines and pyridine N-oxides”, Theor. Exp. Chem., Vol. 36, (2000), pp. 334–337. http://dx.doi.org/10.1023/A:1005220612114[Crossref]
  • [19] V.I. Rybachenko, G. Schroeder, K.Yu. Chotii, E.W. Titov, V.V. Kovalenko, B. Łęska and L.W. Griebieniuk: “Acetyl Exchange between Pyridine N-Oxides in Acetonitrile Solutions: An Attempt to Apply the Marcus Equation to Acetyl Transfer”, Russ. J. Gen. Chem., Vol. 71, (2001), pp. 1608–1615. [Crossref]
  • [20] G. Schroeder, V.I. Rybachenko, K.Yu. Czotii, V.V. Kovalenko, L.W. Griebieniuk, B. Łęska and K. Eitner: “Rate and Equilibrium Constants of Dimethylcarbamoyl Transfer between Pyridine N-Oxides”, Russ. J. Gen. Chem., Vol. 73, (2003), pp. 455–462. http://dx.doi.org/10.1023/A:1024974323588[Crossref]
  • [21] V.I. Rybachenko, G. Schroeder, K.Yu. Czotii, B. Łęska, V.V. Kovalenko and A.N. Redko: “Effect of Acyl Group Structure on Kinetics of Exchange between O-Nucleophiles”, Theor. Exp. Chem., Vol. 39, (2003), pp. 359–363. http://dx.doi.org/10.1023/B:THEC.0000013988.96134.87[Crossref]
  • [22] V.I. Rybachenko, G. Schroeder, V.M. Gokhfel’d, K.Yu. Chotti, V.V. Kovalenko and B. Łęska: “Rate and equilibrium constants of transfer of the dimethylcarbamoyl group between substituted pyridines and their N-oxides”, Russ. J. Gen. Chem., Vol. 74, (2004), pp. 1597–1604. http://dx.doi.org/10.1007/s11176-005-0064-x[Crossref]
  • [23] V.I. Rybachenko, G. Schroeder, K.Yu. Chotii, B. Łęska and A.N. Redko: “Reaction of Acetyl and Benzoyl Chlorides with Pyridines and Pyridine N-Oxides”, Russ. J. Org. Chem., Vol. 40, (2004), pp. 412–416. http://dx.doi.org/10.1023/B:RUJO.0000034981.44740.a5[Crossref]
  • [24] V.I. Rybachenko, G. Schroeder, E.W. Titov, K.Yu. Chotii, R.G. Semenowa and R.A. Makarowa: “Acyl transfer from N-acyl(N-acyloxy)pyridine salts”, Zhurnal Obszcziej Chimii, Vol. 66, (1996), pp. 1007–1011.
  • [25] R. Pankiewicz, G. Schroeder, B. Gierczyk, B. Brzezinski and F. Bartl: “Multinuclear NMR and FTIR studies of new polyoxaalkyl esters of lasalocid and their complexes with lithium and sodium cations”, Biopolymers, Vol. 65, (2002), pp. 95–110. http://dx.doi.org/10.1002/bip.10194[Crossref]
  • [26] G. Schroeder, B. Łęska, B. Gierczyk and V.I. Rybachenko: “Spectroscopic and kinetic characterization of aza-15-crown-5-ether O←N styryl pyridine as Polyfunctional receptor”, Pol. J. Chem., Vol. 75, (2001), pp. 1947–1953.
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  • [28] H. Tsukube, H. Furuta, A. Odani, Y. Takede, Y. Kudo, Y. Inoue, Y. Liu, H. Sakamoto and K. Kimura: “Physical Methods in Supramolecular Chemistry”, In: J.L. Atwood, J.E.D. Davies, D.D. Macnicol and F. Voegtle (Eds.): Comprehensive Supramolecular Chemistry, Elservier Science Ltd., Oxford, 1996, pp. 425–482.
  • [29] M. Bełtowska-Brzezinska, T. Łuczak, B. Gierczyk, K. Eitner, B. Brzezinski, R. Pankiewicz and G. Schroeder: “Studies of lithium and sodium complexation by silicon podand solvents”, J. Mol. Struct., Vol. 607, (2002), pp. 77–86.
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-006-0001-9
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