Scientific Article
previous document  unige:10560  next document
add to browser collection
Title

Effects of charge and intramolecular structure on the lipophilicity of nitrophenols

Authors
Chopineaux-Courtois, V.
Reymond, F.
Bouchard, Géraldine
Testa, Bernard
Girault, H. H.
Published in Journal of the American Chemical Society. 1999, vol. 121, no. 8, p. 1743-1747
Abstract The lipophilicity of a series of phenolic compounds was studied in the 1,2-dichloroethane (1,2-DCE)/water system. Cyclic voltammetry at the ITIES was used to study the transfer characteristics of the charged species, and their partition coefficient was deduced from their formal transfer potential. For the neutral species, log P-DCE values were measured by a two-phase pi-I-metric method. The results are compared to those previously obtained in octanol/water and by linear solvation energy relationships (LSER) in the two solvent systems. It is shown that nitrophenols with intramolecular II-bonding deviate from the solvatochromic equation for the 1,2-DCE/water system, and discrepancies between both approaches are discussed on the basis of conformational and steric effects. When charged however, all the species have approximately the same partition coefficients because the effect of the intramolecular H-bond disappears and the differences in measured lipophilicity arise from the variation of the intramolecular charge delocalization due to resonance equilibria. Some biological implications of these properties are discussed
Stable URL http://archive-ouverte.unige.ch/unige:10560
Full text
Article - document accessible for UNIGE members only Limited access to UNIGE
Other version: http://pubs.acs.org/doi/pdfplus/10.1021/ja9836139
Identifiers
122 hits and 0 download since 2010-08-06
Update
Export document
Format :
Citation style :