Summary
When ionic surfactants are used as mobile phases in micellar liquid chromatography, MLC, the retention of compounds is governed by hydrophobic and electrostatic forces. In the absence of electrostatic effects, the hydrophobicity of a compound is the predominant factor affecting its retention and its interaction with micelles. Because both interactions should be considered for ionic compounds, a novel retention model is proposed which includes the hydrophobicity of a compound and the molar fraction of its charged form. High correlations between the logarithm of the capacity factors and structural parameters were obtained for ionic compounds with different degrees of ionization. The effect of the nature and composition of the mobile phase (pH, concentration of surfactant and modifier) was studied. The modelling of the retention of compounds as a function of physico-chemical parameters and experimental variables was established by means of multivariate regression methods (MLR, PLS). In addition, a predictive model for estimating the hydrophobicity of catecholamines is proposed. Finally, quantitative retention-activity relationships in MLC were also investigated for catecholamines.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
C. Hansch, in E.J. Aries (Editor), Drug Design, Academic Press, New York 1971, Vol. 1.
L. Goldberg (Editor), Structure-Activity Correlation as a Predictive Tool in Toxicology, Hemisphere Publishing, Washington DC, 1983.
C. Hansch, A. Leo, Substituent Constants for Correlation Analysis in Chemistry and Biology, Wiley-Interscience, New York, 1987.
C. Hansch, T. Fujita, J. Am. Chem. Soc.,86, 1616 (1964).
L. G. Danielsson, Y. H. Zhang, Trends Anal. Chem.,15, 188 (1996).
R. Kaliszan, Quantitative Structure-Activity Chromatographic Retention Relationships, Wiley, New York, 1987.
J.G. Dorsey, M.G. Khaledi, J. Chromatogr. A656, 485 (1993).
H. Zou, Y. Zhang, M. Hong, P. Lu, J. Chromatogr. A625, 169 (1992).
D. W. Armstrong, F. Nome, Anal. Chem.53, 1662 (1981).
M. Arunyanart, L. Cline-Love, Anal. Chem.56, 1557 (1984).
M.G. Khaledi, E. Peulr, J. Negh-Ngwainbi, Anal. Chem.,59, 2738 (1987).
F. Gago, J. Alvarez-Builla, J. Elguero, J. C. Diez Masa, Anal. Chem.,59, 921 (1986).
B.K. Lavine, A.J. White J.H. Han J. Chromatogr.542, 29 (1991).
V. Gonzalez, M.A. Rodriguez-Delgado, M.J. Sanchez, F. Garcia-Montelongo, Chromatographia34, 627 (1992).
M.G. Khaledi, E.D. Breyer, Anal. Chem.61, 1040 (1989).
M.L. Marina, M.A. Garcia, J. Chromatogr. A687, 233 (1994).
M.J. Medina-Hernández, M. Catalá Icardo, M.C. Garcia Alvarez-Coque, Chromatographia41, 455 (1995).
M.J. Medina-Hernández, S. Sagrado, J. Chromatogr. A178, 273 (1995).
M.J. Medina-Hernández, M.C. Garcia Alvarez-Coque, Analyst117, 831 (1992).
ACD/logP Method Software (Demo version). Advanced Chemistry Development Inc., 1996, Toronto, Canada.
R.M. Villanueva Camañas, J.M. Sanchis Mallols, J.R. Torres Lapasió, G. Ramis Ramos, Analyst120, 1767 (1995).
H. Martens, T. Naes, Multivariate Calibration, Wiley, New York, 1989.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sanchis Mallols, J.M., Villanueva Camañas, R.M., Sagrado, S. et al. Quantitative retention—structure and retention—activity relationship studies of ionic and non-ionic catecholamines by micellar liquid chromatography. Chromatographia 46, 605–612 (1997). https://doi.org/10.1007/BF02490520
Received:
Revised:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02490520