The reaction of bismuth nitrate pentahydrate, Bi(NO₃)₃·5H₂O, with some heterobifunctional aliphatic thiols

Article type: Research Article

Authors: Ioannou, P.V.

Affiliations: Department of Chemistry, University of Patras, Patras, Greece

Note: [] Corresponding author. Fax: +30 610 997118; E-mail: ioannou@chemistry.upatras.gr

Abstract: The reactions of Bi(NO3)3·5H2O with 11-mercaptoundecanoic acid, L-cysteine, DL-homocysteine, DL-penicillamine and L-glutathione under 1 : 1, 1 : 2, and 1 : 3 mole ratios in the presence of variable amounts of triethylamine were studied. The compounds RS-Bi(NO3)2 were unstable either releasing NO2 or by expelling one NO3− gave cyclic or polymeric products. The compounds (RS)2Bi(NO3) were obtained in the presence of two Et3N but with three Et3N removal of the NO3− lead to polymeric products. The trithiolates were obtained with a 3 : 1 : 3 stoichiometry. A notable exception was the behaviour of DL-penicillamine which gave other than the expected products. The di- and trithiolates are kinetically labile and can add or remove, respectively, thiols. These findings may have biochemical implications when Bi(III) is in a cell.

Keywords: Bismuth nitrate pentahydrate, 11-mercaptoundecanoic acid, L-cysteine, DL-homocysteine, DL-penicillamine, L-glutathione

DOI: 10.3233/MGC-2011-0052

Journal: Main Group Chemistry, vol. 10, no. 3-4, pp. 243-254, 2011