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Title

Solvatochromic analysis of partition coefficients in the o-nitrophenyl octyl ether (o-NPOE)/water system

Authors
Liu, Xiangli
Bouchard, Géraldine
Muller, N.
Girault, H. H.
Testa, Bernard
Published in Helvetica Chimica Acta. 2003, vol. 86, no. 11, p. 3533-3547
Abstract The objective of this study was to unravel the structural properties responsible for the partitioning of solutes in o-nitrophenyl octyl ether (o-NPOE)/H2O, a new solvent system for the determination of the partition coefficients of ions. A set of 88 compounds (including drugs) was selected to allow a regular and broad distribution of property spaces. Partition coefficients in o-NPOE/H2O (log P-npoe)were measured by the shake-flask or the potentiometric method. Linear solvation free-energy relationship (LSER) analyses showed that Van der Waals volume, H-bond-acceptor basicity, and H-bond-donor acidity are the three molecular descriptors of solutes determining their log P-npoc values. The partitioning mechanism of the investigated compounds in oNPOE/H2O is controlled by the same structural properties as it is in 1,2-dichloroethane (DCE)/H2O. Deltalog Values (difference between log P-oct and log P-npoe) express mainly dipolarity/polarizability and H-bond-donor acidity. The solvent o-NPOE is shown to be a good candidate to replace DCE in measurements of lipophilicity
Stable URL http://archive-ouverte.unige.ch/unige:10601
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