A Comparison of the Solvation Properties of 2-Nitrophenyloctyl Ether, Nitrobenzene, andn-Octanol as Assessed by Ion Transfer Experiments

Gulaboski, Rubin and Galland, Alexandra and Bouchard, Géraldine and Caban, Karolina and Kretschmer, Ansgar and Carrupt, Pierre-Alain and Stojek, Zbigniew and Girault, Hubert H. and Scholz, Fritz (2004) A Comparison of the Solvation Properties of 2-Nitrophenyloctyl Ether, Nitrobenzene, andn-Octanol as Assessed by Ion Transfer Experiments. The Journal of Physical Chemistry B, 108 (14). pp. 4565-4572. ISSN 1520-6106

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Official URL: http://dx.doi.org/10.1021/jp037670m

Abstract

The lipophilicity of the anionic forms of drugs and model compounds was assessed by their transfer across (i) the water-2-nitrophenyloctyl ether (NPOE), (ii) the water-nitrobenzene (NB), and (iii) the water-noctanol interfaces by using the three-phase electrode technique. The lipophilicities, expressed in terms of logarithm of partition coefficients, range for the studied anions from -3.46 to 0.68 (log PA-,aq QNPOE) for NPOE, from -3.81 to 2.62 (log PA-,aq QNB ) for NB, and from -6.20 to -3.20 (log PA-,aq Qn-oct) for n-octanol. Although NPOE shares with nitrobenzene the aromatic part and with n-octanol the hydrophobic carbon chain, only very weak correlation was observed between the NPOE-based data with the n-octanol-based data, and the same is true for the correlation of the NB-based and n-octanol-based data. However, there is a strong and even linear correlation between the NPOE-based and the NB-based data.

Item Type: Article
Uncontrolled Keywords: ion transfer, drugs, lipophilicity, biomiometic membranes, Standrad Gibbs energy of ion transfer, thermodynamics
Subjects: Medical and Health Sciences > Basic medicine
Natural sciences > Chemical sciences
Divisions: Faculty of Agriculture
Depositing User: Rubin Gulaboski
Date Deposited: 31 Oct 2012 13:11
Last Modified: 31 Oct 2012 13:11
URI: http://eprints.ugd.edu.mk/id/eprint/147

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