A mechanistic study of the synthesis, single crystal X-ray data and anticarcinogenic potential of bis(2-pyridyl)selenides and -diselenides†
Abstract
The reaction of bis(organyl)diselenide with a reducing agent, such as LiAlH4, NaBH4, Li(C2H5)3BH, etc., generally leads to cleavage of the Se–Se bond resulting in the formation of the corresponding organylselenols/selenolates. However, this work for the first time demonstrates the scisson of the C(pyridine)–Se bond in bis(2-pyridyl)diselenides with LiAlH4. The reaction affords analytically pure bis(2-pyridyl)selenides in near quantitative yields. The reaction pathway involves the formation of a selenated aluminato complex followed by the scission of the C(pyridine)–Se bond and generation of LiAlSeH2. The generation of LiAlSeH2 was established by experimental and NMR analysis. The mechanism of the reaction has been supported by theoretical analysis. Single crystal X-ray structure determination of bis(3-methyl-2-pyridyl)selenide (2e) was performed and it shows that the molecules are self-assembled in a 2D-network of C–H⋯N hydrogen bonds and π⋯π stacking interactions. The synthesized compounds were also evaluated against the Raji cancer cell line (acute lymphoid leukemia).
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