Hydrolysis of the Aquo Ions R3Sn+ and R2Sn+: Steric Effects on the Dissociation of Aquo Acids

Tobias, R. Stuart; Farrer, Humphrey N.; Hughes, Mark B.; Nevett, Brian A.

doi:10.1021/ic50045a048

Cited by 40 publications

(14 citation statements)

References 6 publications

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“…The hydrolysis of this cation in aqueous solution has been studied by several groups. 18,35,36 The hydrolysis constants we determined (Table 2) are in good agreement with those already published, and are taken into consideration during the evaluation of the pH-metric data. The hydroxo complexes formed between pH 2-11.5 were also investigated by means of a pH-dependent 1 H NMR study and the individual NMR parameters (δ, 2 J) of the different hydrolytic species are presented in Table S1 (ESI).…”

Section: Hydroxo Complexes Of Diethyltin(iv)supporting

confidence: 85%

Equilibrium and spectroscopic studies of diethyltin(iv) complexes formed with hydroxymono- and di-carboxylic acids and their thioanalogues

Gajda‐Schrantz

Nagy

Fiore

et al. 2002

J. Chem. Soc., Dalton Trans.

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The complex formation of diethyltin() cation with glycolic (GA), lactic (LA), succinic (SA), malic (MA), tartaric (TA), mercaptoacetic (MAA), 2-mercaptopropionic (MPA), mercaptosuccinic (MSA) and dimercaptosuccinic acid (DMSA) has been investigated by potentiometric, spectrophotometric, 1 H NMR and Mössbauer spectroscopic methods. The mercaptocarboxylic acids yielded much more stable complexes than the corresponding hydroxy acids. Below pH 3, the carboxylate and the still protonated hydroxyl group of hydroxy acids are co-ordinated to the metal ion, while in the case of their thio analogues, {COO Ϫ , S Ϫ } co-ordinated species are dominant. With increasing pH, the metal promoted deprotonation of the hydroxyl group takes place in the presence of MA. In the neutral pH range, among the hydroxy acids, only MA and TA are able to suppress the formation of hydrolytic species of diethyltin(). Although metal co-ordinated water deprotonation was observed around pH 6-7, in the case of the mercaptocarboxylic acids, only ligand-containing complexes were formed in the whole pH range studied. Complexes displaying slow ligand exchange were detected in the case of MA and all mercaptocarboxylic acids, which allowed their structural characterization, by 1 H NMR spectroscopy. In agreement with the Mössbauer spectroscopic data, trigonal bipyramidal, {COO Ϫ , O Ϫ /S Ϫ , OH Ϫ } co-ordinated complexes are dominant around pH 7, with the exception of the octahedral geometry found in the dimer complex M 2 L 2 of DMSA, having a {2COO Ϫ , 2S Ϫ } donor set. Experimental MaterialsDiethyltin() dichloride was purchased from Alfa Aesar. The ligands used are depicted in Scheme 1. They were Merck (MA), Reanal (LA, TA), Sigma (SA, MA, MSA), Aldrich (MAA, MPA) and Fluka (DMSA) products and were used without DALTON

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Section: Hydroxo Complexes Of Diethyltin(iv)supporting

confidence: 85%

Equilibrium and spectroscopic studies of diethyltin(iv) complexes formed with hydroxymono- and di-carboxylic acids and their thioanalogues

Gajda‐Schrantz

Nagy

Fiore

et al. 2002

J. Chem. Soc., Dalton Trans.

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“…However, these experiments were unable to exploit the use of a covalent proteininhibitor complex as reported here. Additional investigations performed at low pH, where the tin chloride bond is broken and a hydrophobic cation is the dominant species in solution (31), indicated that this species binds to the c oligomer and prevents its modification by DCCD. This result is probably due to nonspecific ion pairing of the positive organotin and the negative DCCD-binding amino acid (pK Ϸ 7) in the hydrophobic environment of the membrane.…”

Section: Photoaffinity Labeling Of Atp Synthase and C-oligomer With Dmentioning

confidence: 99%

The ion channel of F-ATP synthase is the target of toxic organotin compounds

Ballmoos

Brunner

Dimroth

2004

Proc. Natl. Acad. Sci. U.S.A.

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ATP is the universal energy currency of living cells, and the majority of it is synthesized by the F 1 F 0 ATP synthase. Inhibitors of this enzyme are therefore potentially detrimental for all life forms. Tributyltin chloride (TBT-Cl) inhibits ATP hydrolysis by the Na ؉ -translocating ATP synthase of Ilyobacter tartaricus or the H ؉ -translocating counterpart of Escherichia coli with apparent K i of 200 nM. To target the site of this inhibition, we synthesized a tritium-labeled derivative of TBT-Cl in which one of the butyl groups was replaced by a photoactivatable aryldiazirine residue. Upon illumination, subunit a of the ATP synthase becomes specifically modified, and this labeling is suppressed in the presence of the original inhibitor. In case of the Na ؉ ATP synthase, labeling is also suppressed in the presence of Na ؉ ions, suggesting an interference in Na ؉ or TBT-Cl binding to subunit a. This interference is corroborated by the protection of ATP hydrolysis from TBT-Cl inhibition by 105 mM Na ؉ . TBT-Cl strongly inhibits Na ؉ exchange by the reconstituted I. tartaricus ATP synthase. Taken together these results indicate that the subunit a ion channel is the target site for ATPase inhibition by toxic organotin compounds. An inhibitor interacting specifically with this site has not been reported previously.

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“…differs from the 31 P NMR chemical shift of the free ligand (δ 28.5) in the same solvent by 14. 5 2)) may hold some potential as model compounds to estimate the coordination environment of the Sn atoms in these complexes.…”

Section: Solution Studiesmentioning

confidence: 99%

Diorganotin dications stabilized by neutral ligands in the solid state: [R2Sn(H2O)2(OPPh3)2](O3SCF3)2 (R = Me, Bu)

et al. 2003

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Hydrolysis of the Aquo Ions R₃Sn⁺ and R₂Sn⁺: Steric Effects on the Dissociation of Aquo Acids

Cited by 40 publications

References 6 publications

Equilibrium and spectroscopic studies of diethyltin(iv) complexes formed with hydroxymono- and di-carboxylic acids and their thioanalogues

Equilibrium and spectroscopic studies of diethyltin(iv) complexes formed with hydroxymono- and di-carboxylic acids and their thioanalogues

The ion channel of F-ATP synthase is the target of toxic organotin compounds

Diorganotin dications stabilized by neutral ligands in the solid state: [R2Sn(H2O)2(OPPh3)2](O3SCF3)2 (R = Me, Bu)

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