Premium
Solvatochromic Analysis of Partition Coefficients in the o ‐Nitrophenyl Octyl Ether ( o ‐NPOE)/Water System
Author(s) -
Liu Xiangli,
Bouchard Géraldine,
Müller Nathalie,
Galland Alexandra,
Girault Hubert,
Testa Bernard,
Carrupt PierreAlain
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390298
Subject(s) - chemistry , partition coefficient , lipophilicity , solvation , ether , solvent , octanol , stereochemistry , chromatography , organic chemistry
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)/H 2 O, 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/H 2 O (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 npoe values. The partitioning mechanism of the investigated compounds in o ‐NPOE/H 2 O is controlled by the same structural properties as it is in 1,2‐dichloroethane (DCE)/H 2 O. Δlog P oct−npoe 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.