Quantitative Structure Retention Relationships of Chloro-N-benzylideneanilines in Normal Phase Liquid Chromatography

Abstract

Quantitative Structure Retention Relationships (QSRRs) of disubstituted N-benzylideneanilines are studied in normal phase liquid chromatography. Structural descriptors for each solute are calculated. Among the descriptors, four are retained to establish the QSRRs. The first descriptor, the dipolar moment is the most important parameter governing the retention, as it represents more than 90% of the log(k′) variation. The influence of three electronic descriptors, ionization potential and Hammett's constants σ_X and σ_Y, is emphasized by the comparison of the QSRRs obtained.

Considering the solvatochromic parameters of the solvants, it appears that hydrogen bond acidic and basic interactions constitute a secondary effect governing the behavior of the solutes. These specific interactions are explained with molecular conformation and charge transfer.