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. 2014 May;122:172-9.
doi: 10.1016/j.talanta.2014.01.048. Epub 2014 Jan 31.

Lipophilicity Indices Derived From the Liquid Chromatographic Behavior Observed Under Bimodal Retention Conditions (Reversed Phase/Hydrophilic Interaction): Application to a Representative Set of Pyridinium Oximes

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Lipophilicity Indices Derived From the Liquid Chromatographic Behavior Observed Under Bimodal Retention Conditions (Reversed Phase/Hydrophilic Interaction): Application to a Representative Set of Pyridinium Oximes

Victor Voicu et al. Talanta. .

Abstract

The liquid chromatographic behavior observed under bimodal retention conditions (reversed phase and hydrophilic interaction) offers a new basis for the determination of some derived lipophilicity indices. The experiments were carried out on a representative group (30 compounds) of pyridinium oximes, therapeutically tested in acetylcholinesterase reactivation, covering a large range of lipophilic character. The chromatographic behavior was observed on a mixed mode acting stationary phase, resulting from covalent functionalization of high purity spherical silica with long chain alkyl groups terminated by a polar environment created through the vicinal diol substitution at the lasting carbon atoms (Acclaim Mixed Mode HILIC 1 column). Elution was achieved by combining different proportions of 5 mM ammonium formiate solutions in water and acetonitrile. The derived lipophilicity indices were compared with logP values resulting from different computational algorithms. The correlations between experimental and computed data sets are significant. To obtain a better insight on the transition from reversed phase to hydrophilic interaction retention mechanisms, the variation of the thermodynamic parameters determined through the van׳t Hoff approach was also discussed.

Keywords: Bimodal chromatographic retention; Lipophilicity indices; Pyridinium oximes.

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