Hydrophobicity Parameters Determined by Reversed-Phase Liquid Chromatography. VII. Hydrogen-Bond Effects in Prediction of the log P Values for Benzyl N, N-Dimethylcarbamates

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The log k' values (k' : capacity factor) of m- and p-substituted benzyl N, N-dimethylcarbamates, I, were obtained by reversed-phase high-performance liquid chromatography (RPLC) on C18-bonded columns with methanol-buffer (pH 7.4) solutions as the mobile phase. The log k_w value, which is considered as a measure of the octanol-water log P value (P : partitoin coefficient), was calculated by linear extrapolation of the plot of log k' against methanol content in eluents. The log k_w values and the k' values at 30,50 and 70% MeOH concentrations were correlated with log P in terms of the hydrogen-bond ability of the substitutent. As is usually observed the amphiprotic substituents, which act as both H-donor and H-acceptor, behaved differently from the others. A log k'-log P plot with very good linearity was obtained with an eluent containing 50% MeOH except for the above mentioned amphiprotic substituents. The log k_w values were much higher than the log P values. This was ascribed to the strong hydrogen accepting ability of the fixed substituent, CH_2 OCONMe_2.
公益社団法人日本薬学会の論文
1993-04-15