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- Title
Solvatochromic Analysis of Partition Coefficients in the o-Nitrophenyl Octyl Ether (o-NPOE)/Water System.
- Authors
Xiangli Liu; Géraldine Bouchard; Nathalie Müller; Alexandra Galland; Hubert Girault; Bernard Testa; Pierre-Alain Carrupt
- 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 Pnpoe) 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 Pnpoe values. The partitioning mechanism of the investigated compounds in o-NPOE/H2O is controlled by the same structural properties as it is in 1,2-dichloroethane (DCE)/H2O. Δlog Poct-npoe Values (difference between log Poct and log Pnpoe) 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.
- Subjects
CHEMICAL structure; PHENOLS; SOLVENTS; PARTITION coefficient (Chemistry)
- Publication
Helvetica Chimica Acta, 2003, Vol 86, Issue 11, p3533
- ISSN
0018-019X
- Publication type
Article