Abstract
The reaction of the proton–deuterium exchange of acetone in imidazolium-based ionic liquid (IL)–deuterium oxide mixtures was studied in detail via NMR spectroscopy. Certain ILs exhibit considerable catalytic properties and contribute to the course of reaction up to the complete deuteration. The efficiency of deuterium exchange crucially depends on the features of ILs; the type of anion and chain length of cation. The linear secondary isotope effects on the NMR chemical shifts of the 13C atoms in acetone were observed depending on the deuteration level of the molecule.
Highlights
Efficient deuterium labelling of organic compounds became a topic of outstanding importance in recent years because of the improved pharmacokinetic properties demonstrated by the Dlabelled drugs.[1,2,3,4,5] On the one hand, the properties of C–H and C–D bonds are very similar, which allows for keeping the desired biological activity of a drug molecule upon C–H/C–D replacement
Our studies showed that under the same conditions, the degree of deuteration in different ionic liquid (IL) was different ranging from complete deuteration to its absence
We report the deuteration of methyl groups in acetone, one of the simplest ketonic compounds, dissolved in IL-D2O mixtures, with the aim of understanding if these mixtures could serve as catalysts and/or hinder the deuterium exchange in solute molecules
Summary
Efficient deuterium labelling of organic compounds became a topic of outstanding importance in recent years because of the improved pharmacokinetic properties demonstrated by the Dlabelled drugs.[1,2,3,4,5] On the one hand, the properties of C–H and C–D bonds are very similar, which allows for keeping the desired biological activity of a drug molecule upon C–H/C–D replacement.
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