A unique case of polymorphism in polyiodide networks resulting from the reaction of the drug methimazole and I2
M. Carla AragoniFirst
;Massimiliano Arca;Alessandra Garau;Francesco Isaia
;Vito Lippolis;Tiziana PivettaLast
2023-01-01
Abstract
The oxidation of thioamide methimazole (C4H6N2S) with molecular diiodine in water afforded the ionic compound [2(C4H5N2S–SN2C4H6)]I3I5 (1) in 1-triclinic and 1-monoclinic polymorphs. The polymorphic nature of [C4H5N2S–SN2C4H6]2I3I5 has been highlighted by comparing the structure of the 1-triclinic form with that of the 1-monoclinic form reported in the literature. No significant geometric differences are observed for the cations in the two polymorphs. The polymorphism is essentially due to a different arrangement in the polyiodide network of the [I5]− and [I3]− components. The FT-Raman spectrum of 1-triclinic shows the characteristic bands in the range 200–50 cm−1 which are in good agreement with the structural features of the polyiodide network. The molecular electrostatic potential maps of the cation methimazole-disulfide [C4H5N2S–SN2C4H6]+ and the bis-cation methimazole-disulfide {[C4H5N2S–SN2C4H6]+}2 in 1-triclinic have been studied to clearly identify the electrostatic potential energy distributions over the cations, and the electron belt and σ-hole areas responsible for the directionality of the non-covalent interactions in the polyiodides. It is suggested that the cation methimazole-disulfide may be a reaction intermediate in the inhibition of thyroid hormones by methimazole.File | Size | Format | |
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NJC unique.pdf Solo gestori archivio
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2.13 MB | Adobe PDF | & nbsp; View / Open Request a copy |
NJ-ART-02-2023-000855_preprint.pdf open access
Type: versione pre-print
Size 4.39 MB
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4.39 MB | Adobe PDF | View/Open |
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