（2007）QSPR Study of Critical Micelle Concentration of Anionic Surfactants Using computational molecular descriptors.pdfVIP

782 J. Chem. Inf. Model. 2007, 47, 782793 QSPR Study of Critical Micelle Concentration of Anionic Surfactants Using Computational Molecular Descriptors† Alan R. Katritzky,*,‡ Liliana Pacureanu,‡ Dimitar Dobchev,‡, and Mati Karelson§, Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, Institute of Chemistry, Tallinn University of Technology, Ehitajate tee 5, Tallinn 19086, Estonia, and Chemistry Department, University of Tartu, 2 Jakobi Street, Tartu 51014, Estonia Received October 27, 2006 A data set of 181 diverse anionic surfactants has been investigated to relate the logarithm of critical micelle concentration (cmc) to the molecular structure using Comprehensive Descriptors for Structural and Statistical Analysis (CODESSA Pro) software. A fragment approach provided superior quantitative structure property relationship (QSPR) models in terms of statistical characteristics and predictive ability. The regression equations provided insight into the structural features of surfactants that influence cmc. The most obvious influence on cmc was manifested by hydrophobic fragments expressed by the topological and geometrical descriptors, while the hydrophilic fragment is represented by constitutional, geometrical, and charge related descriptors. Significantly important molecular descriptors in the selected QSPR models were topological, solvational, and charge-related descriptors as the driving force of the intermolecular interactions between anionic surfactants and water. 1. INTRODUCTION