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Molecular clips based on diphenylglycoluril and benzocrown ethers: promising complexing agents for the alkali metal cations

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Abstract

The interaction of new molecular clips containing diphenylglycoluril and benzocrown ethers moieties with alkali metals ions was studied. Stability constants were determined by spectrophotometric titrations with chloride salts in methanol. Complex stability and cation binding selectivity were shown to be dependent on the size of the crown ether moiety. The “sandwich-type” 1:1 (clip to cation) complexes and the “classical” 1:2 complexes were found. Their ratio varies depending on the molecular clips nature and on the cation type. It was found an unexpected selectivity of the molecular clip with benzo-15-crown-5 moieties toward K+ and Rb+ cations. The molecular structure of the clip complex with benzo-15-crown-5 fragments and sodium picrate was determined by X-ray crystallography. The crystal structure and solution-state structure were proven to be similar.

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Kikot’, L.S., Lyapunov, A.Y., Kulygina, C.Y. et al. Molecular clips based on diphenylglycoluril and benzocrown ethers: promising complexing agents for the alkali metal cations. J Incl Phenom Macrocycl Chem 79, 343–348 (2014). https://doi.org/10.1007/s10847-013-0357-3

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