ESTIMATION OF LIPOPHILICITY OF N-SUBSTITUTED 2-ALKYLIDENE-4-OXOTHIAZOLIDINES BY MEANS OF REVERSED-PHASE THIN-LAYER CHROMATOGRAPHY

Abstract

The chromatographic behavior of 23 new 2-alkylidene-4-oxothiazolidine derivatives was investigated by means of the reversed-phase thin-layer chromatography (RP TLC) on the C₁₈ and CN stationary phases. Binary mixtures of methanol-water, acetonitrile-water, and tetrahydrofuran-water were used as mobile phases. Linear relationships between the volume fraction of the organic mobile phase modifier and the R_M values were established for each solute with high correlation coefficient values (r > 0.99). The investigated 4-oxothiazolidines are a congeneric set of compounds, and significant correlations were obtained between the chromatographically determined and m values. The lipophilicity parameters obtained from the reversed-phase experiments were compared with the calculated log P values. Some of these correlations offer very good predicting models, which are important for a better understanding of the relationships between chemical structure and retention, and can prove helpful in the structure-activity studies as well. Finally, our investigation was focused on chemometric processing of the retention data in different chromatographic systems. To this effect, Principal Component Analysis (PCA) was performed, yielding the results helpful in interpretation of interactions among investigated substances, binary mobile phases, and the two different stationary phases.

Keywords:

• lipophilicity
• principal component analysis
• reversed-phase thin-layer chromatography

ACKNOWLEDGMENT

This work has been supported by the Ministry of Science of Serbia, Grant 142062.

Notes

*A rough bar plot of the eigenvalues.