Quantitative structure–reactivity relationship studies on the catalyzed Michael addition reactions
Bahram Hemmateenejad, Mahmood Sanchooli, Ahmad Reza Mehdipour · Journal of Physical Organic Chemistry · 2008
Abstract Quantitative structure–reactivity relationship (QSRR) can be considered as a variant of quantitative structure–property relationship (QSPR) studies, where the chemical reactivity of reactants or catalysts in a specified chemical reaction is related to chemical structure. In this manner, the Michael addition of some different substrates using different catalysts (SDS, silica gel, and ZrOCl2) was subjected to structure–reactivity relationship, quantitatively. Multiple linear regression (MLR) and partial least square (PLS) were used to perform the QSRR analysis. The resulted models for different catalyzed reactions showed that the catalysts probably act in different mechanisms since the models obtained for the catalysts included different parameters from substrate and enones. Overall, it was found that the reactivity in Michael addition reactions is controlled by coulombic (dipole and charge) interactions as well as the orbital energetic parameters. In the presence of different catalysts, the relative importance of these parameters is changed and hence the catalytic activity is changed. Copyright © 2008 John Wiley & Sons, Ltd.