Unusually short chalcogen bonds involving organoselenium: Insights into the Se-N bond cleavage mechanism of the antioxidant ebselen and analogues

Sajesh Thomas, K. Satheeshkumar, G. Mugesh, T.N. Gururow

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Structural studies on the polymorphs of the organoselenium antioxidant ebselen and its derivative show the potential of organic selenium to form unusually short SeO chalcogen bonds that lead to conserved supramolecular recognition units. SeO interactions observed in these polymorphs are the shortest such chalcogen bonds known for organoselenium compounds. The FTIR spectral evolution characteristics of this interaction from solution state to solid crystalline state further validates the robustness of this class of supramolecular recognition units. The strength and electronic nature of the SeO chalcogen bonds were explored using high-resolution X-ray charge density analysis and atons-in-molecules (AIM) theoretical analysis. A charge density study unravels the strong electrostatic nature of SeO chalcogen bonding and soft-metal-like behavior of organoselenium. An analysis of the charge density around Se-N and Se-C covalent bonds in conjunction with the SeO chalcogen bonding modes in ebselen and its analogues provides insights into the mechanism of drug action in this class of organoselenium antioxidants. The potential role of the intermolecular SeO chalcogen bonding in forming the intermediate supramolecular assembly that leads to the bond cleavage mechanism has been proposed in terms of electron density topological parameters in a series of molecular complexes of ebselen with reactive oxygen species (ROS).
Original languageEnglish
Pages (from-to)6793-6800
JournalChemistry - A European Journal
Volume21
Issue number18
DOIs
Publication statusPublished - 2015

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