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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

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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.

Opis fizyczny
  • 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
  • [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]
  • [2] G. Schroeder, B. Gierczyk and B. Łęska: “Inorganic Esters of Ethylene Glycols Macrocyclic Ligands”, J. Incl. Phenom., Vol. 35, (1999), pp. 327–335. [Crossref]
  • [3] B. Gierczyk, G. Schroeder, G. Wojciechowski, B. Różalski, B. Brzezinski and G. Zundel: “FTIR and multinuclear magnetic resonance studies of tris(oxaalkyl) borates and their complexes with Li+ and Na+ cations”, Phys. Chem. Chem. Phys., Vol. 1, (1999), pp. 4897–4901.[Crossref]
  • [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.[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[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.
  • [8] A. Maia, D. Landini, B. Łęska and G. Schroeder: “Silicon polypodands: a new class of efficient solid-liquid phase-transfer catalysts”, Tetrahedron, Vol. 60, (2004), pp. 10111–10115.[Crossref]
  • [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.[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
  • [11] R. Cacciapaglia and L. Mandolini: “Specific transition state stabilization by metal ions in reactions of functionalized crown ethers”, Pure Appl. Chem., Vol. 65, (1993), pp. 533–538.
  • [12] M. Meng and D.T. Chuang: “Site-directed mutagenesis and functional analysis of the active-site residues of the E2 component of bovine branched-chain alpha-keto acid dehydrogenase complex”, Biochemistry, Vol. 33, (1994), pp. 12879–12885.[Crossref]
  • [13] C.J. O’Connor and R.H. Barton: “Acyl Transfer Isomerization of Glycerol 1,2-Dibutyrate and Propane-1,2-diol 1-Butyrate”, Aust. J. Chem., Vol. 51, (1998), pp. 455–460.
  • [14] Z. Mouloungui and S. Pelet: “Study of the acyl transfer reaction: Structure and properties of glycerol carbonate esters”, Eur. J. Lipid Sci. Tech., Vol. 103, (2001), pp. 216–222. [Crossref]
  • [15] H.K. Oh and J. Jeong: “Kinetics and Mechanism of the animolysis of thiophenyl 2-thiopheneacetates in acetonitrile”, B. Kor. Chem. Soc., Vol. 22, (2001), pp. 1123–1127.
  • [16] I. Lee and D.D. Sung: “Theoretical and Physical Aspects of Stepwise Mechanisms in Acyl-Transfer Reactions”, Curr. Org. Chem., Vol. 8, (2004), pp. 557–567.
  • [17] V.I. Rybachenko, G. Schroeder, B. Łęska, K.Yu. Chotii, R.G. Semenowa, R.A. Makarowa and L.W. Griebieniuk: “Kinetics of dimethylcarbonyl group reaction for N-, O-acylic salt system and theirs oxides”, Theor. Exp. Chem., Vol. 33, (1997), pp. 143–148.
  • [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.[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.[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.[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.[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.[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.[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.
  • [27] R.M. Izatt, J.S. Bradshaw, K. Pawlak, R.L. Breuning and B.J. Tarbet: “Thermodynamic and kinetic data for macrocycle interaction with neutral molecules”, Chem. Rev., Vol. 92, (1992), pp. 1261–1354.[Crossref]
  • [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.
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