Synthesis, X-ray Characterisation and Studies of the New Ionic Complex [Bis(pyridin-2-yl) disulfide] Triiodide, Obtained by Oxidation of 2-Mercaptopyridine with I2 − Implications in the Mechanism of Action of Antithyroid Drugs
✍ Scribed by Constantinos D. Antoniadis; Sotiris K. Hadjikakou; Nick Hadjiliadis; Maciej Kubicki; Ian S. Butler
- Publisher
- John Wiley and Sons
- Year
- 2004
- Tongue
- English
- Weight
- 144 KB
- Volume
- 2004
- Category
- Article
- ISSN
- 1434-1948
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✦ Synopsis
Abstract
The reaction of 2‐mercaptopyridine (C~5~H~5~NS or PYSH) with diiodine in a molar ratio of 1:2 in dichloromethane led to the oxidation and dimerization of the ligand and formation of [(PYS−PYSH)^+^·I~3~^−^]. The compound was characterised by elemental analysis, DTA‐TG, FT‐Raman, FT‐IR, UV/Vis and ^1^H NMR spectroscopy. The crystal structure of the complex has been determined by X‐ray diffraction at 293(2) K. The compound [(C~5~H~4~NS−SNC~5~H~5~)I~3~] is monoclinic with the space group __P__2~1~ and a = 8.230(2) Å, b = 35.708(7) Å, c = 11.369(2) Å, β = 91.86(3)° and Z = 8. The results are discussed in relation to the mechanism of action of antithyroid drugs. The easy oxidation of PYSH by I~2~ to form the monocationic disulfide complex [(PYS−PYSH)^+^·I~3~^−^] is similar to the case of the antithyroid drug methimazole (MMI) and may indicate that PYSH might also possess antithyroid properties similar to those of MMI. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)