Development and validation of a procedure for estimating the hydrophobicity of structurally unrelated compounds by micellar liquid chromatography

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Abstract

Reversed-phase liquid chromatography has been used most often to estimate values of log P, but despite years of study, there is no universally accepted method of performing these estimations. The main problem has to do with the fact that the hydrophobic parameter, log Kw, depends on the hydrogen bond acceptor-donor character of the compounds. The use of micellar mobile phases to perform these estimations is evaluated here, and the influence of the nature of the surfactant (anionic, cationic, and nonionic) on the log k-log P relationships is studied. The use of a nonionic surfactant, such as Brij35, to prepare the mobile phases provided adequate results regardeless of the hydrogen bond acceptor-donor character of the compounds, whereas noncongener behaviors are found with anionic and cationic surfactants. This enabled the establishment of a calibration set consisting of 7 compounds with variable hydrophobicity in order to calibrate new columns and predict log P values. In these conditions, the hydrophobicity of structurally unrelated compounds in the -0.1 < log P < 4.5 range can be measured. To evaluate the accuracy of predictions, the hydrophobicity of 27 compounds is determined and compared with the log P values calculated using the ACD-log P program. Nonsignificant differences between the predicted and the theoretical log P values were achieved at 95% probability level.

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Beleña-Pozo, I., Villanueva-Camañas, R. M., Sagrado, S., & Medina-Hernández, M. J. (1999). Development and validation of a procedure for estimating the hydrophobicity of structurally unrelated compounds by micellar liquid chromatography. Journal of Chromatographic Science, 37(10), 375–382. https://doi.org/10.1093/chrsci/37.10.375

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