The reaction of BAL with Sn(IV), SnCl2·2H2O, Pb(II), Ag(I), Cd(II) and Pd(II) gave water-insoluble solids where BAL coordinated using its two sulfur atoms, BAL(S,S)M, while anhydrous SnCl2 gave BAL(O,S)Sn. Apart from the Sn(IV) and Ag(I) which should be monomeric, the structure of the other solids (monomeric or polymeric) could not be established. Indium(III) chloride did not react with either thiophenol or BAL in the absence of a base. In the presence of sodium hydroxide under 1:1:1, 1:2:2 and 1:3:3 molar ratios of InCl3/PhSH/NaOH, the products incorporated the formed sodium chloride and In(SPh)3 was isolated after aqueous work up in the 1:3:3 case. Thallium(III) aceteate gave Tl-SPh and PhSSPh. Thallium(I) acetate and thallium(I) fluoride also gave Tl-SPh in 100% and 75% yields, respectively. The lower yields with TlF is attributed to the non thiophilic HTlF2 formed during the reaction. Theoretical calculations of TlF, (TlF)2 and TlF2- revealed a novel structure of (TlF)2 and shed light to the non thiophilicity of TlF2-. Thallium(I) acetate and BAL gave the expected bis salt while the reactions of TlF under various stoichiometries of BAL:TlF were complicated. Summarizing these and previous results it seems that BAL cannot detoxify heavy metal cations by forming water soluble complexes.
AnisuzzamanA.K.M. and OwenL.N., Dithiols. Part XXIII. Optically active forms of 2,3-dimercaptopropanol and related thiols, J Chem Soc C (1967), 1021–1026.
2.
BerasteguiP. and HullS., The crystal structure of thallium(I) fluoride, J Solid State Chem150 (2000), 266–275.
3.
BonomiF., PaganiS., CariatiR., PozziA., GrisponiG., CristianiF., DiazA. and ZanoniR., Synthesis and characterization of metal derivatives of dihydrolipoic acid and dihydrolipoamide, Inorg Chim Acta192 (1992), 237–242.
4.
BrownD.S., EinsteinF.W.B. and TuckP.G., Tetragonal pyramidal indium(III) species. The crystal structure of tetraethylammonium pentachloroindate(III), Inorg Chem8 (1969), 14–18.
5.
BrownD.H., McKinlayG.C. and SmithW.E., Some complexes of 2,3-dimercaptopropanol (BAL) with gold(I) and gold(III), J Inorg Biochem10 (1979), 275–279.
6.
Canal NetoA. and
JorgeF.E., All-electron double zeta basis sets for the most fifth-row atoms: Application in DFT spectroscopic constant calculations, Chem Phys Lett582 (2013), 158–162.
7.
Canal NetoA.,
MunizE.P.,
CentoducatteR. and JorgeF.E., Gaussian basis sets for correlated wave functions. Hydrogen, helium, first- and second-row atoms, J Mol Struct (Theochem)718 (2005), 219–224.
8.
CantyA.J. and KishimotoR., Mercury(II) and organomercury(II) complexes of thiols and dithiols, including British Anti-Lewisite, Inorg Chim Acta24 (1997), 109–122.
9.
CatschA. and Harmuth HoeneA.-E., New developments in metal antidotal properties of chelating agents, Biochem Pharmacol24 (1975), 1557–1562.
10.
CatschA. and Harmuth HoeneA.-E., Pharmacology and therapeutic applications of agents used in heavy metal poisoning, Pharmacol Ther A1 (1976), 1–118.
11.
ChadhaR.K., HayesP.C., MabroukH.E. and TuckD.G., Coordination compounds of indium. Part 43. Indium(III) derivatives of benzenethiol, and the crystal structure of tetraphenylphosphonium bromotris(benzenethiolato)-indate(III), Ph4P[BrIn(SPh)3], Can J Chem65 (1987), 804–809.
12.
DehmerJ.L., BerkowitzJ. and CusachsL.C., Photoelectron spectroscopy of high temperature vapors. III. Monomer and dimer spectra of thallous fluoride, J Chem Phys58 (1973), 5681–5686.
13.
DomangeL., Fluor, in Nouveau Traité de Chimie Minérale (
PascalP. editor), 1960, Masson et cie, Paris, vol. XVI, pp. 29–37, 131–133.
14.
FellerD., The role of databases in support of computational chemistry calculations, J Comp Chem17 (1996), 1571–1586.
15.
FreemanR., GasserR.P.H., RichardsR.E. and WheelerD.H., Chemical shifts of thallium resonance spectra in solutions of thallous salts, Mol Phys2 (1959), 75–84.
GilmanH. and AbbottR.K.Jr., Characterization of sulfonic, sulfinic, phosphinic and some other acids as thallous salts, J Am Chem Soc71 (1949), 659–660.
18.
HeardP.J., Main group dithiocarbamate complexes, Progress Inorg Chem53 (2005), 1–69.
19.
HeineJ., HolyńskaM., ReuterM., HaasB., ChatterjeeS., KochM., GriesK.I., VolzK. and DehnenS., In(SAr)3 as a building block for 3D and helical coordination polymers, Cryst Growth Design13 (2013), 1252–1259.
20.
IoannouP.V., Dimethylphosphinato and dimethylarsinato complexes of group 13 metals and their chemistry, Monatsh Chem144 (2013), 793–802.
21.
IoannouP.V. and TsivgoulisG.M., Thiolates of arsenic(III), antimony(III), and bismuth(III) with DL-α-dihydrolipoic acid, Monatsh Chem145 (2014), 897–909.
22.
IoannouP.V. and TsivgoulisG.M., The reaction of dithioerythritol and dithiothreitol with As(III), Sb(III), and Bi(III) compounds, Monatsh Chem146 (2015), 249–257.
23.
IoannouP.V., VachliotisD.G. and KouliO., The reaction of British Anti-Lewisite (dimercaptol) with As(III), Sb(III), and Bi(III) oxides and salts, Main Group Chem12 (2013), 235–249.
24.
KenesheaF.J. and CubicciottiD., The thermodynamics of vaporization of thallous fluoride and its gaseous dimerization, J Phys Chem69 (1965), 3910–3915.
25.
KrebsB. and BrömmelhausA., TlSPh and TlSBu, thallium(I) thiolates with novel cagelike structural units: [Tl5(SPh)6]- [Tl7(SPh)6]+ and [Tl8(SBu)8], Angew Chem Int Ed Engl28 (1989), 1682–1683.
26.
KrężelA.,
LeśniakW.,
Jeżowska-BojczukM.,
MłynarzP.,
BrasuñJ.,
KozłowskiH. and BalW., Coordination of heavy metals by dithiothreitol, a commonly used thiol group protectant, J Inorg Biochem84 (2001), 77–88.
27.
LeeA.G., The Chemistry of Thallium, 1971, Elsevier, Amsterdam, p. 28.
28.
LeussingD.L., The reaction of nickel(II) with 2,3-dimercapto-1-propanol, J Am Chem Soc82 (1960), 4458–4481.
29.
LeussingD.L. and JayneJ., Mononuclear and polynuclear complex formation between iron(II) and 2,3-dimercapto-1-propanol, J Phys Chem66 (1962), 426–429.
30.
LeussingD.L. and TischerT.N., Mononuclear and polynuclear complex formation by manganese(II) and zinc(II) ions with 2,3-dimercapto-1-propanol: The behavior of the Er function with mercaptide, J Am Chem Soc83 (1961), 65–70.
31.
MoJ., EomD., KimS.H. and LeeP.H., Palladium-catalyzed carbon-sulfur cross-coupling reactions of aryl chlorides with indium tris(organothiolates), Chem Letters40 (2011), 980–982.
32.
OrdM.G. and StockenL.A., A contribution of chemical defence in World War II, Trends Biochem Sci25 (2000), 253–256.
33.
PascalP., Indium, in Nouveau Traité de Chimie Minérale (
PascalP. editor), 1961, Masson et cie, Paris, vol. VI, pp. 839–843.
34.
PeppeC. and TuckD.G., Coordination compounds of indium. Part 42. The insertion of indium(I) halides into homonuclear bonds in non-aqueous media, Can J Chem62 (1984), 2798–2802.
35.
PetersR.A., StockenL.A. and ThompsonR.H.S., British Anti-Lewisite (BAL), Nature156 (1945), 616–619.
36.
ReissO.K., Pyruvate metabolism, II. Restoration of pyruvate utilization in heart sarcosomes by α-(+)-lipoic acid, J Biol Chem233 (1958), 789–793.
37.
RemyH., Treatise on Inorganic Chemistry, (translated by
AndersonJ. S.), 1956, Elsevier, Amsterdam, vol II, p. 399.
38.
SchluterR.D., KräuterG. and ReesW.S., Metal thiolate compounds: Processable ceramic precursors, J Cluster Sci8 (1997), 123–154.
39.
SchuchardtK.L., DidierB.T., ElsethagenT., SunL., GurumoorthiV., ChaseJ., LiJ. and WindusT.L., Basis set exchange: A community data base for computational sciences, J Chem Inf Model47 (2007), 1045–1052.
40.
StevensonK.J., GaleH. and PerhamR.N., Inhibition of pyruvate dehydrogenase multienzyme complex from Escherichia coli with mono- and bifunctional arsenoxides, Biochemistry17 (1978), 2189–2192.
41.
StockenL.A. and ThompsonR.S., Reactions of British Anti-Lewisite with arsenic and other metals in living systems, Physiol Rev29 (1949), 168–192.
42.
StreetsD.G. and BerkowitzJ., The structure of Tl2F2 from photoelectron spectroscopy, Chem Phys Letters38 (1976), 475–478.
TranquardA., CoffyG. et
BoinonM.-J., Le système binaire eau - fluorure de thallium, Bull Soc Chim France (1969), 2608–2610.
45.
VilenskyJ.A. and RedmanK., British Anti-Lewisite (dimercaprol): An amazing history, Ann Emerg Med41 (2003), 378–383.
46.
WadeK. and BanisterA.J., Aluminium, Gallium, Indium and Thallium, in Comprehensive Inorganic Chemistry, (BailarJ. C.Jr,
EmeléusH. J.,
NyholmR. and Trotman-DickensonA. F. editors), 1973, Pergamon Press, Oxford, Vol. 1, p. 1107.
47.
WebbE.C. and van HeyningenR., The action of British Anti-Lewisite (BAL) on enzyme systems, Biochem J41 (1947), 74–78.
48.
WestR.C., CRC Handbook of Chemistry and Physics, 65th Edition, 1984, CRC Press, Boca Raton, FL.
49.
ZumanP. and ZumanováR., Polarographische studie der reactionen des 2:3-dimercaptopropanols (BAL) mit schwermetallen und einigen oxydationsmitteln, Tetrahedron1 (1957), 289–300.
