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 nucleophile 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.