The application of computational techniques to medicinal chemistry is growing at a tremendous rate. Quantitative structure-activity relationships (QSAR), which relate biological and toxicological activities to structural features, have been employed widely to correlate structure to activity. A difficulty of this approach has been nonuniformity of parameter sets and the inability to examine contributions across properties and data sets. Linear solvation energy relationships (LSER) developed by Kamlet and Taft circumvent many of the difficulties and successfully utilize a single set of parameters for a wide range of physical, chemical, and biological properties. We have replaced the LSER solvato-chromatic parameters with theoretically determined parameters to permit better a priori prediction of properties. Comparison of the two parameter sets for five biological activities is presented, showing the excellent fit of the theoretically determined parameters.
The application of computational techniques to biology, chemistry and physics is growing rapidly. Quantitative structure–activity relationships (QSAR) have been used widely to relate biological activities and physicochemical properties to molecular structural features. A difficulty in this approach has been non‐uniformity of parameter sets resulting in the inability to examine contributions across properties and data sets. Linear solvation energy relationships (LSER) developed by Kamlet and Taft successfully utilize a single set of parameters to correlate a wide range of biological, chemical and physical properties. The empirical LSER solvatochromic parameters have been replaced with theoretically determined parameters to permit greater ease in a priori property prediction. These TLSER descriptors have given good correlations and interpretations for some biological activities. This paper discusses the application of these descriptors to six physicochemical properties involving equilibria, kinetics and spectra. The results show good correlation and physical interpretation.
ABSTRACT:In an effort to model solute-solvent interactions, the C=O stretching frequencies of five 1-substituted 2-pyrrolidinones and four other carbonyl-containing compounds were measured for 30 common solvents. These were then correlated with four empirical parameter sets and one theoretical (computational) parameter set. While an empirical parameter set gave the best correlation equations, the theoretical parameter equations are physically and statistically significant. Solvent volume, polarizability and hydrogen bond donor acidity (capacity) terms are significant in the correlation equations.
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