Approaches to Lipophilicity Methods and

Pierre-Alain Carnipt, Bernard Testa, and Patrick Gaillard 

Institut de Chimie Therapeutique, BEP, Universite de Lausanne, CH-1015 Lausanne-Dorigny, Switzerland 

Reviews in Computational Chemistry, Volume 11 Kenny B. Lipkowitz and Donald B. Boyd, Editors Wiley-VCH, John Wiley and Sons, Inc., New York, 1997 

Lipophilicity is a molecular property defined as the logarithm of the partition coefficient (i.e., log P) of a solute between two essentially immiscible solvent phases. Partition coefficients are obtained as a ratio of concentrations at equilibrium  

As discussed later, the values and physicochemical meaning of this parameter change from one organic solvent to another. By definition, partition coefficients apply to solutes in a single, well-defined electrical state. Most published partition coefficients are those of neutral species, whereas the accurate measurement of the log F values of ions and zwitterions remains a current challenge. As such, partition coefficients must be carefully discriminated from distribution coefficients (log D), which apply to ionizable solutes at a given pH and are thus the combined expression of the lipophilicity of at least two ionic species in a pH-dependent proportion.  

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Carrupt, P.-A., Testa, B., Gaillard, P. Computational approaches to lipophilicity methods and applications. Rev. Computat. Chem. 1997, 11, 241-315. 

Pierre-Alain Carrupt, Bernard Testa, and Patrick Gaillard, Computational Approaches to Lipophilicity Methods and Applications. 

Lipophilicity in Molecular Modeling. See also, P.-A. Carrupt, B. Testa, and P. Gaillard, in Reviews in Computational Chemistry, K. B. Lipkowitz and D. B. Boyd, Eds., Wiley-VCH, New York, 1997, Vol. 11, pp. 241-315. Computational Approaches to Lipophilicity Methods and Applications. 

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