Retention Behavior of Compounds with Active Hydrogen Atoms
and Their Acetylated Derivatives in Reversed-Phase HPLC

I. G. Zenkevich and V. M. Kosman

St. Petersburg Institute of Chemistry and Pharmacology, ul. Professora Popova 14, St. Petersburg, 197376 Russia

Received April 8, 1996

Abstract—In view of poor interlaboratory reproducibility of retention indices I in reversed-phase high-perfor-
mance liquid chromatography, not the indices themselves but their differences for reactants and products of
interaction with various reagents can be used to identify compounds with active hydrogen atoms. For acetylated
derivatives of phenols and aromatic amines, the quantity I = I(ArXH) –I(ArXCOCH₃), where X = O or NH,
has statistically significant distinguishable values of 126 15 and 70 20, respectively. The additivity of the
parameters I is first revealed for the polyfunctional compounds of these classes that are incapable of intramo-
lecular hydrogen bonding. Abnormal I values and deviations from the additivity rule are observed only for
substances with intramolecular hydrogen bonding. This finding can be used to confirm the presence of relevant
structural units in molecules.

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