An approach to the extreme in separation science : recognition of isotopic chirality

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(1) Phenyl(pentadeuterophenyl)methanol (I) having isotopic chirality was prepared. Enantiomers of (I) were independently prepared.(2) A 60 cm column system packed with cellulose tribenzoate-coated silica was prepared.(3) The separation of a racemic mixture of (1) as well as diphenylmethanol and di(pentadeuterophenyl)-methanol was achieved for the first time at the 60 cycle on the column system.(4) The stationary phase was found to possess a binding site which preferentially binds a deuterated phenyl group over a phenyl group.(5) Various stationary phases with functional groups for reversed-phase liquid chromatography were prepared(6) Various H/D isotopic compounds were chromatographed, and the separation examined.(7) Aromatic stationary phases, especially those having heavy atoms, showed high isotopic recognition, indicating that the dispersion interaction is the major mechanism of isotopic recognition.(8) The results suggest that the cellulose stationary phase possesses a binding site for deuterated phenyl group which has lower polarizability, and another one with higher polarizability.(9) This study made it possible to understand the mechanism of isotope recognition and the isotope effect of hydrophobic interaction.(l0)Similar approach will be useful to elucidate chiral recognition mechanisms.