Determination of the lipophilicity of some aniline derivatives by reversed-phase thin-layer chromatography. The effect of the organic phase in the eluent

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Abstract

The lipophilicity of aniline and 36 ring-substituted aniline derivatives was determined by reversed-phase thin-layer chromatography using methanol, acetone and acetonitrile as the organic phase. The RM value of each compound linearly decreased with increasing concentration of the organic solvent, Acetonitrile showed the highest and methanol the lowest solvent strength, however, the difference between the solvent strength of methanol and acetone was negligible. The site of the substitution considerably influenced the lipophilicity particularly in the case of -NO2 groups. Good correlation was found between the RM value extrapolated to zero organic phase concentration and the partition coefficient between n-octanol:water. The change in the RM value caused by a 1% increase of the organic phase concentration also correlated with the partition coefficient, however, it was of secondary importance. The lipophilicity parameters determined by reversed-phase thin-layer chromatography correlated to a lesser extent with the calculated lipophilicity values of aniline derivatives.

Original languageEnglish
Pages (from-to)318-322
Number of pages5
JournalChromatographia
Volume18
Issue number6
DOIs
Publication statusPublished - Jun 1 1984

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Keywords

  • Aniline derivatives
  • Lipophilic character
  • TLC reversed-phase

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

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