Equilibrium and Multinuclear NMR Spectroscopic Studies of Di- and Trimethyltin(IV) Moieties with Hydroxycarboxylic Acids in Aqueous Medium

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• 作者：Mridula ; Mala Nath
• 关键词：Hydroxycarboxylic acids ; Organotin ; Potentiometric ; NMR studies
• 刊名：Journal of Solution Chemistry
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：45
• 期：3
• 页码：445-462
• 全文大小：523 KB
• 参考文献：1.Nath, M., Eng, G., Song, X., Beraldo, H., De Lima, G.M., Pettinari, C., Marchetti, F., Whalen, M.M., Beltrán, H.I., Santillan, R., Farfán, N.: Medicinal/biocidal applications of tin compounds and environmental aspects. In: Davies, A.G., Gielen, M., Pannell, K.H., Tiekink, E.R.T. (eds.) Tin Chemistry, Fundamentals, Frontiers, and Applications, 1st edn., Chap. 4. Wiley, London (2008)
  2.Appel, K.E.: Organotin compounds: toxicokinetic aspects. Drug Metab. Rev. 36, 763–786 (2004)CrossRef
  3.Pagliarani, A., Trombetti, F., Ventrella, V. (eds.): Biochemical and Biological Effects of Organotins, 1st edn. Bentham Science, Sharjah (2012)
  4.Champ, M.A.: A review of organotin regulatory strategies, pending actions, related costs and benefits. Sci. Total Environ. 258, 21–71 (2000)CrossRef
  5.Frache, R., Rivaro, P.: Occurrence, pathways and bioaccumulation of organometallic compounds in marine environments. In: Gianguzza, A., Pellizzetti, E., Sammartano, S. (eds.) Chemical Processes in Marine Environment, 1st edn., Chap. 10. Springer, Berlin (2000)
  6.Gianguzza, A., Giuffrè, O., Piazzese, D., Sammartano, S.: Aqueous solution chemistry of alkyltin(IV) compounds for speciation studies in biological fluids and natural waters. Coord. Chem. Rev. 256, 222–239 (2012)CrossRef
  7.De Stefano, C., Foti, C., Gianguzza, A., Marrone, F., Sammartano, S.: Hydrolysis of methyltin(IV) trichloride in aqueous NaCl and NaNO3 solutions at different ionic strengths and temperatures. Appl. Organomet. Chem. 13, 805–811 (1999)CrossRef
  8.De Stefano, C., Foti, C., Gianguzza, A., Martino, M., Pellerito, L., Sammartano, S.: Hydrolysis of (CH3)2Sn2+ in different ionic media: salt effects and complex formation. J. Chem. Eng. Data 41, 511–515 (1996)CrossRef
  9.Hynes, M.J., Keely, J.M., McManus, J.: Investigation of the hydrolysis of [Sn(CH3)3(H2O)2]+ in aqueous solution by Tin-119 Nuclear Magnetic Resonance spectroscopy. J. Chem. Soc. Dalton Trans 12, 3427–3429 (1991)CrossRef
  10.Cigala, R.M., De Stefano, C., Giacalone, A., Gianguzza, A., Sammartano, S.: Hydrolysis of monomethyl-, dimethyl-, and trimethyltin(IV) cations in fairly concentrated aqueous solutions at I = 1 mol·L−1 (NaNO3) and T = 298.15 K. Evidence for the predominance of polynuclear species. J. Chem. Eng. Data 56, 1108–1115 (2011)CrossRef
  11.De Stefano, C., Foti, C., Gianguzza, A., Millero, F.J., Sammartano, S.: Hydrolysis of (CH3)3Sn+ in various salt media. J. Solution Chem. 28, 959–972 (1999)CrossRef
  12.El-Sherif, A.A.: Solution coordination chemistry of organotin(IV) cations with bio-relevant ligands. J. Solution Chem. 41, 1522–1554 (2012)CrossRef
  13.Takahashi, A., Natsume, T., Koshino, N., Funahashi, S., Inada, Y., Takagi, H.D.: Speciation of trimethyltin(IV): hydrolysis, complexation equilibria, and structures of trimethyltin(IV) ion in aqueous solution. Can. J. Chem. 75, 1084–1092 (1997)CrossRef
  14.Mohamed, M.M.A., Shoukry, M.M.: Interaction of diphenyltin(IV) dichloride with some selected bioligands. Chem. Pharm. Bull. 49, 253–257 (2001)CrossRef
  15.Nath, M., Kompelli, N.: Speciation and NMR spectrometric studies of interaction of di- and triorganotin(IV) moieties with 5′-guanosine monophosphate and guanosine in aqueous solution. J. Solution Chem. 43, 1184–1204 (2014)CrossRef
  16.Nath, M., Jairath, R., Mukherjee, G.N., Das, A.: Speciation of dimethyltin(IV) and trimethyltin(IV) cations with some biologically important ligands in aqueous medium: a potentiometric investigation. Indian J. Chem. 44A, 1602–1607 (2005)
  17.Nath, M.: Sulaxna.: potentiometric and multinuclear NMR investigations of di-/trimethyltin(IV) cations with some heterocyclic thiones in aqueous media. New J. Chem. 31, 418–428 (2007)CrossRef
  18.Jankovics, H., Nagy, L., Kele, Z., Pettinari, C., D’Agati, P., Mansueto, C., Pellerito, C., Pellerito, L.: Coordination properties of the ACE inhibitor captopril towards Me2Sn(IV)2+ in aqueous solution, and biological aspects of some dialkyltin(IV) derivatives of this ligand. J. Organomet. Chem. 668, 129–139 (2003)CrossRef
  19.Pellerito, L., Nagy, L.: Organotin(IV)n+ complexes formed with biologically active ligands: equilibrium and structural studies, and some biological aspects. Coord. Chem. Rev. 224, 111–150 (2002)CrossRef
  20.Buck-Koehntop, B.A., Porcelli, F., Lewin, J.L., Cramer, C.J., Veglia, G.: Biological chemistry of organotin compounds: interactions and dealkylation by dithiols. J. Organomet. Chem. 691, 1748–1755 (2006)CrossRef
  21.Gielen, M.: Tin based anti-tumour drugs. Coord. Chem. Rev. 151, 41–51 (1996)CrossRef
  22.Siebenlist, K.R., Taketa, F.: Interactions of triethyltin bromide with components of the red cell. Toxicol. Appl. Pharmacol. 58, 67–75 (1981)CrossRef
  23.Ali, A.A., Upreti, R.K., Kidway, A.M.: Interaction of di- and tributyltin chloride with human erythrocyte membrane. Toxicol. Appl. Pharmacol. 38, 13–18 (1987)
  24.Jancsó, A., Nagy, L., Moldrheim, E., Sletten, E.: Potentiometric and spectroscopic evidence for coordination of dimethytin(IV) to phosphate groups of DNA fragments and related ligands. J. Chem. Soc. Dalton Trans. 10, 1587–1594 (1999)CrossRef
  25.Hynes, M.J., Dowd, M.O.: Interactions of the trimethyltin(IV) cation with carboxylic acids, amino acids, and related ligands. J. Chem. Soc. Dalton Trans. 3, 563–566 (1987)CrossRef
  26.Buzás, N., Gajda, T., Kuzmann, E., Nagy, L., Vértes, A., Burger, K.: Coordination properties of l -cysteine and its derivatives towards diethyltin(IV) in aqueous solution. Main Group Met. Chem. 18, 641–649 (1995)CrossRef
  27.Capolongo, F., Giuliani, A.M., Giomini, M., Russo, U.: Interactions of organotin(IV) halides with reduced glutathione in aqueous solution. J. Inorg. Biochem. 49, 275–293 (1993)CrossRef
  28.Furlán, R.L.E., Mata, E.G., Mascaretti, O.A.: Efficient, non-acidolytic method for the selective cleavage of N-Boc amino acid and peptide phenacyl esters linked to a polystyrene resin. J. Chem. Soc. Perkin Trans. 1, 355–358 (1998)CrossRef
  29.Szorcsik, A., Nagy, L., Gyurcsik, B., Vankó, G., Krämer, R., Vértes, A., Yamaguchi, T., Yoshida, K.: Organotin(IV) complexes of polyhydroxyalkyl carboxylic acids and some related ligands. J. Radioanal. Nucl. Chem. 260, 459–469 (2004)CrossRef
  30.Arena, G., Gianguzza, A., Pellerito, L., Musumeci, S., Purrello, R., Rizzarelli, E.: Co-ordination properties of dialkyltin(IV) in aqueous solution. Thermodynamics of complex formation with carboxylic acids. J. Chem. Soc. Dalton Trans. 8, 2603–2608 (1990)CrossRef
  31.Fiore, T., Foti, C., Gianguzza, A., Orecchio, S., Pellerito, L.: D-glucuronate complexes of mono-, di- and triorganotin(IV) compounds: potentiometric and Mössbauer spectroscopic investigations. Appl. Orgamomet. Chem. 16, 294–301 (2002)CrossRef
  32.AlAlousi, A.S., Shehata, M.R., Shoukry, M.M., Mohamed, N.N.: Interaction of dimethyltin(IV) and trimethyltin(IV) with dehydroacetic acid. Chem. Spec. Bioavailab. 21, 1–6 (2009)CrossRef
  33.Gajda-Schrantz, K., Nagy, L., Fiore, T., Pellerito, L., Gajda, T.: Equilibrium and spectroscopic studies of diethyltin(IV) complexes formed with hydroxymono- and di-carboxylic acids and their thioanalogues. J. Chem. Soc., Dalton Trans 2, 152–158 (2002)CrossRef
  34.Cardiano, P., Giuffrè, O., Napoli, A., Sammartano, S.: Potentiometric, 1H NMR and ESI-MS investigation on dimethyltin(IV) cation–mercaptocarboxylate interaction in aqueous solution. New J. Chem. 33, 2286–2295 (2009)CrossRef
  35.Jansco, A., Gajda, T., Szorcsik, A., Kiss, T., Henry, B., Vanko, G., Rubini, P.: Potentiometric and spectroscopic studies on the dimethyltin(IV) complexes of 2-hydroxyhippuric acid. J. Inorg. Biochem. 83, 187–192 (2001)CrossRef
  36.Fazio, S.A., Uhlinger, D.J., Parker, J.H., White, D.C.: Estimations of uronic acids as quantitative measures of extracellular and cell wall polysaccharide polymers from environmental samples. Appl. Environ. Microbial. 43, 1151–1159 (1982)
  37.Christensen, B.E., Kjosbakken, J., Smidsrod, O.: Partial chemical and physical characterization of two extracellular polysaccharides produced by marine, perphytic pseudomonas sp. strain NCMB 2021. Appl. Environ. Microbial. 50, 837–845 (1985)
  38.Guard, H.E., Coleman III, W.M., Ross, M.M.: On the characterization of the reaction of organotin compounds with D-glucuronic acid. Carbohydr. Res. 235, 41–51 (1992)CrossRef
  39.Putten, P.L.: Mandelic acid and urinary tract infections. A. Van Leeuw. 45, 622–623 (1979)CrossRef
  40.Taylor, M.B.: Summary of mandelic acid for the improvement of skin conditions. Cosmet. Dermatol. 21, 26–28 (1999)
  41.Kroes, B.H., van den Berg, A.J., Quarles van Ufford, H.C., Van Dijk, H., Labadie, R.P.: Anti-inflammatory activity of gallic acid. Planta Med 58, 499–504 (1992)CrossRef
  42.Inoue, M., Suzuki, R., Sakaguchi, N., Li, Z., Takeda, T., Ogihara, Y., Jiang, B.Y., Chen, Y.: Selective induction of cell death in cancer cells by gallic acid. Biol. Pharm. Bull. 18, 1526–1530 (1995)CrossRef
  43.Uozakia, M., Yamasaki, H., Katsuyama, Y., Higuchi, M., Higuti, T., Koyama, A.H.: Antiviral effect of octyl gallate against DNA and RNA viruses. Antiviral Res. 73, 85–91 (2007)CrossRef
  44.Kubola, J., Siriamornpun, S.: Phenolic contents and antioxidant activities of bitter gourd (Momordica charantia L.) leaf, stem and fruit fraction extracts in vitro. Food Chem. 110, 881–890 (2008)CrossRef
  45.Nath, M., Vats, M., Roy, P.: Design, spectral characterization, anti-tumor and anti-inflammatory activity of triorganotin(IV) hydroxycarboxylates, apoptosis inducers: in vitro assessment of induction of apoptosis by enzyme, DNA-fragmentation, acridine orange and comet assays. Inorg. Chim. Acta 423, 70–82 (2014)CrossRef
  46.Sizova, T.V., Yashina, N.S., Petrosyan, V.S., Yatsenko, A.V., Chernyshev, V.V., Aslanov, L.A.: X-ray structure investigation of trimethyltin α-phenyl-α-oxoacetate. J. Organomet. Chem. 453, 171–174 (1993)CrossRef
  47.Gajda-Schrantz, K., Nagy, L., Kuzmann, E., Vértes, A.: Coordination sphere symmetry of di-n-butyltin(IV) complexes containing ligands with O, O donor atoms. J. Radioanal. Nucl. Chem. 232, 151–158 (1998)CrossRef
  48.Terra, V.R., Barbiéri, R.S., CasteloBranco, P.A., Abras, A.: Synthesis and characterization of compounds diorganoestânicos acid dl-mandelic acid. Eclet. Chem. 23, 17–30 (1998)
  49.Kohn, R., Kováč, P.: Dissociation constants of d -galacturonic and d -glucuronic acid and their O-methyl derivatives. Chem. Zvesti. 32, 478–485 (1978)
  50.Cruywagen, J.J., Rohwer, E.A.: Equilibria and thermodynamic quantities for the reactions of molybdenum(VI) and tungsten(VI) with mandelate (α-hydroxybenzeneacetate). J. Chem. Soc. Dalton Trans. 21, 3433–3438 (1995)CrossRef
  51.Beltrán, J.L., Sanli, N., Fonrodona, G., Barrón, D., Özkan, G., Barbosa, J.: Spectrophotometric, potentiometric and chromatographic pKa values of polyphenolic acids in water and acetonitrile–water media. Anal. Chim. Acta 484, 253–264 (2003)CrossRef
  52.Natsume, T., Aizawa, S., Hatano, K., Funahashi, S.: Hydrolysis, polymerization and structure of dimethyltin(IV) in aqueous solution. Molecular structure of the polymer [(SnMe2)2(OH)3]ClO4. J. Chem. Soc. Dalton Trans. 19, 2749–2753 (1994)CrossRef
  53.Caldeira, M.M., Ramos, M.L., Oliveira, N.C., Gil, V.M.S.: Complexes of vanadium(V) with α-hydroxycarboxylic acids studied by 1H, 13C, and 51V nuclear magnetic resonance spectroscopy. Can. J. Chem. 65, 2434–2440 (1987)CrossRef
  54.Portanova, R., Lajunen, L.H.J., Tolazzi, M., Pisspanen, J.: Critical evaluation of stability constants for α-hydroxycarboxylic acid complexes with protons and metal ions and the accompanying enthalpy changes–Part II: aliphatic 2-hydroxycarboxylic acids. Pure Appl. Chem. 75, 495–540 (2003)CrossRef
  55.Bermejo, E., Carballo, R., Castiñeiras, A., Lago, A.B.: Coordination of α-hydroxycarboxylic acids with first-row transition ions. Coord. Chem. Rev. 257, 2639–2651 (2013)CrossRef
  56.Lockhart, T.P., Manders, W.F.: Structure determination by NMR spectroscopy. Correlation of [ 2 J(119Sn-1H)] and the Me–Sn–Me angle in methyltin(IV) compounds. Inorg. Chem. 25, 892–895 (1986)CrossRef
  57.Surdy, P., Rubini, P., Buzás, N., Henry, B., Pellerito, L., Gajda, T.: Interaction of dimethyltin(IV)2+ cation with Gly-Gly, Gly-His, and some related ligands. A new case of a metal ion able to promote peptide nitrogen deprotonation in aqueous solution. Inorg. Chem. 38, 346–352 (1999)CrossRef
  58.Holeček, J., Nádvorník, M., Handlíŕ, M., Lyčka, A.: 13C and 119Sn NMR spectra of di-n-butyltin(IV) compounds. J. Organomet. Chem. 315, 299–308 (1986)CrossRef
  
• 作者单位：Mridula (1)
  Mala Nath (1)
  
  1. Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand, 247 667, India
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Physical Chemistry
  Industrial Chemistry and Chemical Engineering
  Geochemistry
  Oceanography
  Inorganic Chemistry
  Condensed Matter
  
• 出版者：Springer Netherlands
• ISSN：1572-8927

文摘

The complex formation of [Me₂Sn]2+/[Me₃Sn]+ with glucuronic [(HL-1)], mandelic [(HL-2)] and gallic [(HL-3)] acids has been studied potentiometrically in aqueous solution (I = 1.0 mol·dm−3 KNO₃, 298 ± 0.1 K) and the speciation of various complex species has been evaluated as a function of pH. The results show that these hydroxycarboxylic acid ligands (HL) coordinate via the deprotonated oxygen atom of the carboxylate group resulting in the formation of mixed hydroxo species [Me₂Sn(L)(OH)] (12.6–46.2 % in 1:1, 18.3–64.0 % in 1:2) along with [Me₂Sn(L)]+ (9.2–18.0 % in 1:1, 14.8–27.8 % in 1:2) in Me₂Sn(IV)–(HL) systems and single 1:1 species [Me₃Sn(L)] (7.1–12.2 % in 1:1, 13.2–21.7 % in 1:2) in Me₃Sn(IV)–(HL) systems at acidic pHs. At physiological pH ~7.0, the major species is [Me₂Sn(OH)₂] (96.0–97.5 % in 1:1, 92.4–97.2 % in 1:2) with minor amount of [Me₂Sn(L)(OH)] (0.4–2.5 % in 1:1, 1.0–5.8 % in 1:2) in Me₂Sn(IV)–(HL) systems. Similarly, in Me₃Sn(IV)–(HL) systems the major species formed is [Me₃Sn(OH)] (86.6–91.5 % in 1:1, 84.7–89.3 % in 1:2) with a very small amount of [Me₃Sn(L)] (1.0–1.4 % in 1:1, 1.7–3.0 % in 1:2). At pH >8.0, only hydroxo species are formed, viz. [Me₂Sn(OH)₂], [Me₂Sn(OH)₃]− and [Me₃Sn(OH)]. In all of the systems, no polymeric species were observed in the studied pH range. Multinuclear (1H, 13C and 119Sn) NMR studies, carried out at different pHs, confirmed the species formation and led us to propose their possible geometries in aqueous solution.