New stationary phase for liquid chromatography with chemically bonded pinane ligand: synthesis and characterization by nuclear magnetic resonance andhigh-performance liquid chromatographic investigations

A new bicyclic phase for liquid chromatography was prepared by solution pol ymerization approaches. To introduce a C-4 spacer the starting molecule 3-f ormylpinane was reduced to the alcohol followed by a substitution of the hy droxy group through a bromide. The obtained halide reacted with magnesium a nd allyl bromide to the 3-(but-3'-enyl)pinane which was hydrosilylated with trichlorosilane and finally immobilized to silica gels with different pore sizes using the technique of solution polymerization. To elucidate the str ucture of 3-(but-3'-enyl)pinane high-resolution two-dimensional nuclear mag netic resonance (NMR) spectra were carried out. The new phases were charact erized, on the one hand by employing C-13 and Si-29 solid-state NMR spectro scopy and on the other hand, by separating a standard test mixture consisti ng of mainly monosubstituted aromatic compounds. The results achieved in ch romatography were correlated with the information gained from Si-29 CP/MAS NMR measurements. (C) 2000 Elsevier Science B.V. All rights reserved.