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Butyltin(IV) citrates and tartrates: Structural characterization and their interaction with nucleotides

Published on Apr 1, 2013in Journal of Organometallic Chemistry2.066
· DOI :10.1016/J.JORGANCHEM.2013.01.015
Hanna Pruchnik11
Estimated H-index: 11
(Wroclaw University of Environmental and Life Sciences),
Florian P. Pruchnik19
Estimated H-index: 19
(UWr: University of Wrocław)
Abstract
Abstract Butyltin complexes with biologically important hydroxyacids, citric HOOCCH 2 C(OH)(COOH)CH 2 COOH (C 6 H 8 O 7 ) acid and (2 R ,3 R )-(+)-tartaric HOOCCH(OH)CH(OH)COOH (C 4 H 6 O 6 ) acid: [Sn(C 4 H 9 ) 2 (C 6 H 6 O 7 )] ( 1 ), [Sn(C 4 H 9 ) 3 (C 6 H 7 O 7 )] ( 2 ), (phenH) 2 [Sn(C 4 H 9 ) 3 (C 6 H 5 O 7 )] ( 3 ), [Sn(C 4 H 9 ) 2 (C 4 H 4 O 6 )] ( 4 ), [Sn(C 4 H 9 ) 3 (C 4 H 5 O 6 )] ( 5 ), (phenH)[Sn(C 4 H 9 ) 3 (C 4 H 4 O 6 )] ( 6 ) and [{Sn(C 4 H 9 ) 3 } 2 (C 4 H 4 O 6 )] ( 7 ) have been synthesized and characterized by ESI–MS, IR and 1 H, 13 C and 119 Sn NMR spectra. Their structures and properties in solid state and solutions were proposed on the basis of the spectroscopic data and density functional theory (DFT) calculations at B3LYP/3-21G** level. Complexes in solutions in polar solvents are five-coordinate as evidenced by 13 C and 119 Sn NMR spectra. Geometries of the five-coordinate complexes were optimized with B3LYP/3-21G** calculations. The 13 C, 31 P and 119 Sn NMR spectra prove that complexes effectively interact with AMP, ATP and DAMP nucleotides forming Sn–OP bonds and N⋯H–O (nucleotide–carboxylate ligand) hydrogen bonds. In the case of dibutyltin complexes ( 1 and 4 ) nucleotides may also be coordinated as a chelating ligands via phosphate group and N7 atom of adenine residue.
  • References (45)
  • Citations (6)
References45
Newest
#1Hanna Pruchnik (Wroclaw University of Environmental and Life Sciences)H-Index: 11
#2Małgorzata Latocha (Medical University of Silesia)H-Index: 13
Last. Florian P. Pruchnik (UWr: University of Wrocław)H-Index: 19
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Abstract Butyltin complexes with 5-sulfosalicylic acid (H 3 ssal) [Sn(C 4 H 9 ) 3 {O 3 SC 6 H 3 (OH)COOH}] ( 1 ), [Sn 2 (C 4 H 9 ) 6 (OOCC 6 H 3 OHSO 3 )] ( 2 ) and [Sn 3 (C 4 H 9 ) 6 (OOCC 6 H 3 (OH)SO 3 ) 2 O] ( 3 ) have been synthesized and characterized by ESI-MS, IR and 1 H, 13 C and 119 Sn NMR spectra. Their structures and properties in solid state and solutions were proposed on the basis of the spectroscopic data and density functional theory (DFT) calculations at B3LYP/3-21G ∗∗ level. Th...
10 CitationsSource
#1Hanna Pruchnik (Wroclaw University of Environmental and Life Sciences)H-Index: 11
#2Tadeusz Lis (UWr: University of Wrocław)H-Index: 33
Last. Florian P. Pruchnik (UWr: University of Wrocław)H-Index: 19
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Abstract Three butyltin complexes with 2-sulfobenzoic acid [Sn(C 4 H 9 ) 2 {O 3 SC 6 H 4 COO-2}(H 2 O)]·(C 2 H 5 OH) ( 1 ), [Sn(C 4 H 9 ) 3 {O 3 SC 6 H 4 COOH-2}] ( 2 ) and [Sn 2 (C 4 H 9 ) 6 {μ-O 3 SC 6 H 4 COO-2}] ( 3 ) have been synthesized and characterized by IR and 1 H, 13 C and 119 Sn NMR spectra. They show interesting properties in solid state and solutions because there are many modes of coordination of the Sbz ligand. The structure of complex 1 has been determined by X-ray crystallogra...
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#2Estefanía Carrasco-García (Universidad Miguel Hernández de Elche)H-Index: 10
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Abstract We studied the Sn(IV)-complex, [Sn(C 6 H 4 O 7 ) 2 ] 2− formed after anodic dissolution of a tin surface through its passive oxide film in citric–citrate aqueous solution buffer pH 3. Tin-complex was experimentally characterized using infrared spectroscopy while ab initio calculations were made to study its structure and vibrational properties. These calculations gave us a precise knowledge of the normal modes of vibration taking into account that in the complex the molecule comprises a...
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A novel class of tartaric acid-derived N-spiro quaternary ammonium salts was synthesised starting from known TADDOLs. These compounds were found to catalyse the asymmetric α-alkylation of glycine Schiff bases with high enantioselectivities and in good yields.
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#1Vaso Dokorou (UoI: University of Ioannina)H-Index: 10
#2Alexandra Primikiri (UoI: University of Ioannina)H-Index: 4
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#1Tushar S. Basu Baul (NEHU: North Eastern Hill University)H-Index: 24
#2Anup Paul (NEHU: North Eastern Hill University)H-Index: 16
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Abstract A series of tributyltin(IV) complexes based on 2/4-[( E )-2-(aryl)-1-diazenyl]benzoate ligands was synthesized, wherein the position of the carboxylate and aryl substituents (methyl, tert -butyl and hydroxyl) varies. The complexes, Bu 3 SnL 1–4 H ( 1 – 4 ), have been structurally characterized by elemental analysis and IR, NMR ( 1 H, 13 C, and 119 Sn) and 119 Sn Mossbauer spectroscopy. All have a tetrahedral geometry in solution and a trigonal bipyramidal geometry in the solid-state, ex...
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Tin compounds and their therapeutic potentials are under consideration from many research groups, while a number of early reviews recording advances in the screening for antiproliferative potential of organotins are also available. This review focuses upon results obtained on the antiproliferative activity of tin compounds in the past 5 years.
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