Iodo( trisyl) sulfane: Reactivity of a Stable Alkanesulfenyl Iodide towards Antithyroid Drugs

Wismach, Cathleen and Jones, Peter G and du Mont, Wolf-Walther and Mugesh, Govindasamy and Papke, Ulrich and Linden, H Bernhard and Arca, Massimiliano and Lippolis, Vito (2014) Iodo( trisyl) sulfane: Reactivity of a Stable Alkanesulfenyl Iodide towards Antithyroid Drugs. In: EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2014 (8). pp. 1399-1406.

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Abstract

Iodination of tris(trimethylsilyl)methanethiol (trisylthiol, TsiSH) in tetrahydrofuran provides the new thermally stable alkanesulfenyl iodide iodo(trisyl)sulfane, TsiSI] as a violet solid. Iodo(trisyl)sulfane exhibits iodine-iodine contacts between pairs of TsiSI molecules in the solid state. Properties of TsiSI were studied by vibrational spectroscopy and with the help of density functional calculations. TsiSI reacts in the presence of triethylamine with the antithyroid drugs 6-n-propyl- and 6-methylthiouracil (PTU, MTU) and with N-methylmethimazole (MMI) to form unsymmetric disulfides that were investigated by means of X-ray crystallography. In the solid state, the PTU and MTU derivatives exist as hydrogen-bonded centrosymmetric dimers, whereas the MMI-derived disulfide is an unsymmetric monomer.

Item Type:	Journal Article
Publication:	EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
Publisher:	WILEY-V C H VERLAG GMBH
Additional Information:	Copyright for this article belongs to the WILEY-V C H VERLAG GMBH, BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY
Keywords:	Medicinal chemistry; Iodine; Sulfanes; Density functional calculations
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	24 Jun 2014 07:37
Last Modified:	24 Jun 2014 07:37
URI:	http://eprints.iisc.ac.in/id/eprint/49327

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