Comparison of physicochemical and gas chromatographic polarity measures for simple organic compounds

K. Heberger, Igor G. Zenkevich

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

The comparison of different polarity measures (parameters, descriptors, variables, scales, etc.) indicates that evaluation of interrelations between these measures is important for better understanding and interpretation of chemical and/or analytical data, especially for chromatographic separation. The best linear correlation between gas chromatographic and non-chromatographic polarity descriptors is revealed for the first time: this pair of variables is the difference of gas chromatographic retention indices on standard polar and non-polar phases as well as the difference between non-dimensional indices of boiling points (known in chromatography since mid-1980s as dispersion indices) and indices of molar refractions. The correlation helps chromatographers to find preferable chemical variables (features) to understand better the separation phenomena and to find better correlations in QSRR models. Principal component analysis (PCA) of ten frequently applied polarity measures shows their similarity and, at the same time, it shows the absence of anomalies within the set of simple organic molecules. A novel ranking method for ten polarity parameters points out that the two most informative polarity measures are (i) the non-dimensional index for boiling point and (ii) the difference in chromatographic retention indices on standard polar and non-polar stationary phases. On the other hand, the hydrophobicity parameter, log P, sometimes considered as polarity parameter in HPLC seems to be the worst one in description of "polarity" in gas chromatography. Surprisingly, such polarity measures like dipole moment and permittivity used often in organic chemistry does not provide the best correlation with gas chromatographic polarity measures.

Original languageEnglish
Pages (from-to)2895-2902
Number of pages8
JournalJournal of Chromatography A
Volume1217
Issue number17
DOIs
Publication statusPublished - Apr 2010

Fingerprint

Organic compounds
Gases
Boiling point
Organic Chemistry
Dipole moment
Hydrophobicity
Chromatography
Principal Component Analysis
Refraction
Hydrophobic and Hydrophilic Interactions
Gas chromatography
Gas Chromatography
Principal component analysis
Permittivity
High Pressure Liquid Chromatography
Molecules

Keywords

  • Chemometrics
  • Gas chromatography
  • HPLC
  • Physicochemical constants
  • Polarity measures
  • Principal component analysis
  • QSRR
  • Ranking
  • Retention indices

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Biochemistry
  • Medicine(all)

Cite this

Comparison of physicochemical and gas chromatographic polarity measures for simple organic compounds. / Heberger, K.; Zenkevich, Igor G.

In: Journal of Chromatography A, Vol. 1217, No. 17, 04.2010, p. 2895-2902.

Research output: Contribution to journalArticle

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