Contribution of Substituents to the Distribution Coefficient of N-Benzoyl-N-phenylhydroxylamine Derivatives.

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  • INOUE Sadanobu
    Department of Material Science, Kitami Institute of Technology
  • UTO Masayuki
    Department of Material Science, Kitami Institute of Technology

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Abstract

The distribution coefficient (KD) for twenty kinds of N-benzoyl-N-phenylhydroxylamine (BPHA) derivatives between chloroform or benzene and the aqueous phase was determined. A linear correlation was obtained between log KD and the number of carbon atoms containing substituent groups for a series of alkyloxy derivatives. However, the data for those having a series of alkyloxy groups, and others having a straight or branched alkyl chain, fall on two independent lines in plots of log KD vs. the van der Waals volume of the BPHA derivatives. From these results, the empirical contribution values (πx), defined asπx=log KD(X)-log KD(H) {KD(H) is the distribution coefficient of a parent compound and KD(X) that of a derivative}, of the functional group to the distribution coefficient (log KD), were as follows: 0.54 in a chloroform/ water system and 0.49 in a benzene/water system for the methyl and methylene groups, 0.30 in a chloroform/water system and 0.27 in a benzene/water system for the methoxy group, and -0.23 in a chloroform/water system and -0.12 in a benzene/water system for the nitro group, respectively. The utility of the contribution values (πx) for the methyl, methylene, methoxy and nitro groups was verified for estimating the distribution coefficient (KD) of the BPHA derivatives.

Journal

  • Analytical Sciences

    Analytical Sciences 11 (5), 723-728, 1995

    The Japan Society for Analytical Chemistry

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