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Iodo(trisyl)sulfane: Reactivity of a Stable Alkanesulfenyl Iodide towards Antithyroid Drugs
Author(s) -
Wismach Cathleen,
Jones Peter G.,
du Mont WolfWalther,
Mugesh Govindasamy,
Papke Ulrich,
Linden H. Bernhard,
Arca Massimiliano,
Lippolis Vito
Publication year - 2014
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201301576
Subject(s) - chemistry , iodide , iodine , triethylamine , tetrahydrofuran , reactivity (psychology) , solid state , molecule , monomer , halogenation , trimethylsilyl , medicinal chemistry , photochemistry , inorganic chemistry , organic chemistry , polymer , medicine , alternative medicine , pathology , solvent
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.