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Abstract
A RP-HPLC procedure has been developed for measuring the capacity factor k' of a series of new 5-substituted-2-amino-2-oxazolines. the chromatographic behaviour measured on a μBondapack C18 column with methanol-aqueous buffer as mobile phase was related to the volume fraction of methanol φ. the log k' value extrapolated to 0% organic modifier in the eluent (log k'w) was chosen as a measure of the solute lipophilicity. A good correlation was found between the slope S and the intercept value (log k'w) of the log k' versus φ straight lines for all these structurally related 2-amino-2-oxazolines.
Some parameters related either to chromatographic conditions or to chemical structure were shown to influence the capacity factor. A study made at different pH values indicated that log k'w increased with the basicity of the mobile phase.
The influence of the eluent pH on the capacity factor of 2-amino-2-oxazolines was related to their pKa's values determined by a potentiometric method.
Since log k' is considered as a valuable indice of the lipophilicity, the determined values will be used for quantitative structure-activity relationship studies of these new class of structurally related compounds