MULTIVARIATE CHARACTERIZATION AND MODELING OF THE CHEMICAL-REACTIVITY OF EPOXIDES

The chemical reactivity of epoxides is an important determinant for their toxic effects. The issue of modeling the chemical reactivity toward the nucteophile 4-nitrobenzylpyridine (NBP) of a series of 15 epoxides is addressed. For this purpose a multivariate characterization of their chemical and structural properties is carried out using quantum chemical molecular orbital calculations. By means of partial least-squares projections to latent structures (PLS), a set of nine theoretical descriptors is found to be sufficiently informative for modeling the reactivity with NBP. Two calculated quantitative structure-property relationships (QSPRs) are also shown to exhibit sound predictive capabilities.