Mercury(II) and Organomercury(II) Complexes of Thiols and Dithiols, Including British Anti-Lewisite

Abstract

The dithiols 2,3-dimercapto-l-propanol (British anti-Lewisite) and 1,3-dimercapto-2propanol form complexes RHgS-SHgR (R = Me, Ph). The PhHg(II) complexes decompose in benzene and methanol at ambient temperature to form diphenylmercury. A 1:1 complex of Hg(II) with 1,3 dimercapto-2-propano1 is dimeric in pyridine. Infrared, Raman, and 1H NMR spectra of RHg(II) and Hg(II) dithiol complexes are compared with those of PhHgSR (R = Me, Et, H, But, Ph, CH,CH20H) and Hg(SR')2 (R’ = Me, Et, But, Ph, CH2CH20H). Phenylmercury(II) thiolates have the coupling constant J(orthoH-199Hg) within the range 144-155 Hz. The complexes PhHgSR and Hg(SR”)z (R” = Et, But, Ph) are monomeric in chloroform; the chloroform insoluble complexes Hg(SR”')2 (R”’ = Me, CH,CH20H) and organomercury (II) dithiolates are monomeric in pyridine. Aspects of the use of British anti-Lewisite as an antidote for mercury poisoning are discussed.