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http://dx.doi.org/10.5012/bkcs.2002.23.1.065

The Hydroxyl Group-Solvent and Carbonyl Group-Solvent Specific Interactions for Some Selected Solutes Including Positional Isomers in Acetonitrile/Water Mixed Solvents Monitored by HPLC  

Cheong, Won-Jo (Department of Chemistry and Center for Advanced Bioseparation Technology and Institute of Industrial Biotechnology, Inha University)
Keum, Young-Ik (Department of Chemistry and Center for Advanced Bioseparation Technology and Institute of Industrial Biotechnology, Inha University)
Ko, Joung-Ho (Department of Chemistry and Center for Advanced Bioseparation Technology and Institute of Industrial Biotechnology, Inha University)
Publication Information
Bulletin of the Korean Chemical Society / v.23, no.1, 2002 , pp. 65-70 More about this Journal
Abstract
We have evaluated the specific hydroxyl group-solvent and carbonyl group-solvent interactions by using an Alltima C18 stationary phase and by measuring the retention data of carefully selected solutes in 60/40, 70/30, and 80/20(v/v%) acetonitrile/water eluents at 25, 30, 35, 40, 45, and 50 oC. The selected solutes are phenol, acetophenone, alkylbenznes(benzene to hexylbenznene), 4 positional isomers of phenylbutanol, 5-phenyl-1-pentanol, 3 positional isomers of alkylarylketone derived from butylbenzene, and 1-phenyl-2-hexanone. The magnitudes of hydroxyl group-acetonitrile/water specific interaction enthalpies are larger than those of carbonyl group-acetonitrile/water specific interaction enthalpies in general while the magnitudes of carbonyl group-methanol/water specific interaction enthalpies are larger than those of hydroxyl group-methanol/water specific interactions. We observed clear discrepancies in functional group-solvent specific interaction among positional isomers. The variation trends of solute transfer enthalpies and entropies with mobile phase composition in the acetonitrile/water system are much different from those in the methanol/water system. The well-known pocket formation of acetonitrile in aqueous acetonitrile mixtures has proven to be useful to explain such phenomena.
Keywords
Carbonyl group; Hydroxyl group; Specific interaction; Aqueous acetonitrile; Positional isomers;
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