Reaction of pharmacological active tris-(2-hydroxyethyl)ammonium 4-chlorophenylsulfanylacetate with ZnCl(2) or NiCl(2): first conversion of a protic ionic liquid into metallated ionic liquid

The reaction of pharmacological active protic ionic liquid tris-(2-hydroxyethyl)ammonium 4-chlorophenylsulfanylacetate H(+)N(CH(2)CH(2)OH)(3) ∙ ((-)OOCCH(2)SC(6)H(4)Cl-4) (1) with zinc or nickel chloride in a ratio of 2:1 affords stable at room temperature powder-like adducts [H(+)N(CH(2)CH(2)OH)(3)](2) ∙ [M(OOCCH(2)SC(6)H(4)Cl-4)(2)Cl(2)](2-), M = Zn (2), Ni (3). By recrystallization from aqueous alcohol compound 2 unexpectedly gives Zn(OOCCH(2)SC(6)H(4)Cl-4)(2) ∙ 2H(2)O (4). Unlike 2, compound 3 gives crystals [N(CH(2)CH(2)OH)(3)](2)Ni(2+) · [(-)OOCCH(2)SC(6)H(4)Cl-4](2) (5), which have a structure of metallated ionic liquid. The structure of 5 has been proved by X-ray diffraction analysis. It is the first example of the conversion of a protic ionic liquid into potentially biological active metallated ionic liquid (1 → 3 → 5).