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 σX and σY, 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.