Abstract
The determination of the lipophilicity of 3,3,5-trimethyl-1-azocycloheptane- and 1,3,3-trimethyl-6-azobicyclo[3.2.1]octane derivatives by reversed-phase thin-layer chromatography shows marked anomalies. In ion-free eluent systems the R M values show an extremely small dependence on the proportio of organic solvent solvent in the mobile phase. A logarithmic relationship was found between the R M value and the pH of the eluent system. The effect of ion concentration can be modelled by a polynomial function. These anomalies can be explained by the change in the ion-pair formation of the very hydrophilic quaternary ammonium group and by the change in the solvate shell around the very lipophilic organic part of the molecule caused by different pH values and by different ion concentrations.
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