Determination of the lipophilicity of fused-ring nitrogen heterocycles by reversed-phase thin-layer chromatography. The effect of pH

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Abstract

The lipophilicity (R(M) value) and specific hydrophobic surface area of 21 fused-ring nitrogen heterocycles has been determined by reversed-phase thin-layer chromatography and the effect of different mobile-phase additives such as acetic acid, sodium acetate, and lithium chloride on the retention has been studied. Regular retention behavior was observed for each solute, the R(M) value decreasing linearly with increasing concentration of acetonitrile in the mobile phase. Retention was reduced by acetic acid and increased by lithium chloride and sodium acetate, acetic acid having the strongest effect. The solute lipophilicity and specific hydrophobic surface area values for each mobile phase could be intercorrelated, indicating the homologous character of the fused-ring nitrogen heterocycles under acidic, alkaline, and neutral conditions. Spectral mapping showed clustering of the solutes according to the number of rings in the molecules, indicating that the ring structures are planar and that they lie on the hydrophobic surface of the stationary phase.

Original languageEnglish
Pages (from-to)64-69
Number of pages6
JournalJournal of Planar Chromatography - Modern TLC
Volume11
Issue number1
Publication statusPublished - Jan 1 1998

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Keywords

  • Fused-ring nitrogen heterocycles
  • Lipophilicity
  • Reversed-phase thin-layer chromatography
  • Specific hydrophobic surface area

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry

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