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1 1998

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Sole Buntego - zapomniane związki

Orzeszko A., Kazimierczuk Z.

Wiadomości Chemiczne

1998

[Z] 52, 1-2

125-135

This paper is devoted to organic thiosulfates, so called Bunte salts. On the occasion of the 150th anniversary of Hans Bunte's birth (1848), the short biographical note was annexed. The main, historical method of synthesis of organic thiosulfate was described with some novel modification [3-11]. In Figs 1 and 2 the general structure of Bunte salts and the mentioned reaction are shown, respectively. Newer methods of synthesis like, for example, the addition of thiosulfate anion to alkenes or oxiranes are presented in Figs 3 and 5 [2,12, 13, 18, 19]. In the next chapter some chemical properties of Bunte salts were described . Aqueous solutions of these compounds are unstable. In acid medium they hydrolyse to thiols, while in basic one to appropriate disulfides (Figs 6, 7) [3,10, 22-26]. The reaction of dihalides with sodium thiosulfate leads to 'double' Bunte salts carrying two thiosulfate end groups. It was found that in presence of NaOH or H2O2 these salts give appropriate polydisulfides [8, 9]. The scheme of this process is shown in Fig. 11. It was found that anodic oxidation of Bunte salts leads also to di - and polydisulfides [7]. Usually, organic sulphur compounds show strong biological activity. There are a few examples of biological studies on organic thiosulfates in the literature. The sodium ethylthiosulfate, originally prepared by Bunte [3], exhibits a striking synergistic affect with the bacteriostatic 2-mercaptobenzothiazole against Staphylococcus aureus and tubercle bacillus [43, 44]. Sodium salt of the aromatic 3-nitrophenylthiosulfate was reported to show strong preventive and curative activity against fowl coccidiosis [22]. Radioprotective properties of heterocyclic derivatives of thiosulfates were also investigated [48]. The chemical structure of Bunte salt anions carrying a long aliphatic chain suggests their amphiphilic character. It is known that amphiphility of numerous quaternary ammonium salts is responsible for their ability to damage cell membranes. We paid our attention to the relationship between the chemical structure and the antibacterial and fungicidal activity of a number of known and newely synthesised Bunte salts [7]. The results of this work are presented in Fig. 13. Many Bunte salts have excellent technical applications described in the patents cited [42-49].