Liquid Chromatographic Study of Solute Hydrogen Bond Basicity

Lay Choo Tan, Peter W. Carr*, Jean Frechet, Vladimir Smigol

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

The purpose of the present work was to investigate a liquid chromatographic method for the measurement of relative hydrogen bond basicities of dilute species. This type of determination cannot be done with conventional reversed-phase liquid chromatography due to the silanophilic interactions of basic solutes with the silica packing material. The studies were done on a polymeric stationary phase with pendant phenol groups that act as powerful hydrogen bond donors. Solute retention was evaluated in terms of two hydrogen bond basicity scales, β2H and β2C, and a steric hindrance parameter, E β2H and β2C are basicity scales based on the free energy of forming 1:1 hydrogen bond complexes and the retention on a strong hydrogen bond donor gas chromatographic phase, respectively. The Es parameter characterizes the steric effect experienced by the solute acceptor site. It is shown that retention correlates very strongly with β2Hand less strongly with β2C. The log k′ values need only two descriptive parameters, i.e., β2Hand Es to give a good fit. As a whole, retention on the phenolic polymeric phase provides an efficient method for the measurement of relative hydrogen bond basicities.

Original languageEnglish (US)
Pages (from-to)450-457
Number of pages8
JournalAnalytical Chemistry
Volume66
Issue number4
DOIs
StatePublished - Feb 15 1994

ASJC Scopus subject areas

  • Analytical Chemistry

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