Gas Chromatographic Studies of Interactions Between Selected Organic Nucleophiles and the NMR Shift Reagent, Tris(1,1,1,2,2,3,3-heptafluoro-7,7-dimethyl-4,6-octanedionato)europium(III)

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Abstract
Tris(1,1,1,2,2,3,3-heptafluoro-7,7-dimethyl-4,6-octanedionato) europium(III), Eu(fod)3, in squalane solution was used as a liquid phase in a GC examination of the interactions of selected ketones and alcohols with Eu(fod)3. The relative stabilities of the complexes formed between the ketones and alcohols and the Eu(fod)3 chelate can be explained in terms of donating abilities of the nucleophiles and steric constraints of the interactions. In general, the alcohols form more stable complexes with Eu(fod)3 than do the ketones. The alcohol-metal chelate interaction is much more critically affected by steric crowding than is the ketone-metal chelate interaction. An isotope effect has been observed for the interaction between deuterated alcohols and Eu(fod)3 where the deuteration is geminal to the hydroxyl group. As a result of this isotope effect, a difference of 3.5% was observed in the retention times of 2-butanol and d1 2-butanol. These results indicate that the deuterated species form more stable complexes with Eu(fod)3 than do the non-deuterated species.

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