Bond-based global and local (bond, group and bond-type) quadratic indices and their applications to computer-aided molecular design. 1. QSPR studies of diverse sets of organic chemicals

摘要

The concept of atom-based quadratic indices is extended to a series of molecular descriptors (MDs) (both total and local) based on adjacency between edges. The kth edge-adjacency matrix (E-k) denotes the matrix of bond-based quadratic indices (non-stochastic) with respect to the canonical basis set. The kth "stochastic" edge-adjacency matrix, ESk, is here proposed as a new molecular representation easily calculated from E-k. Then, the kth stochastic bond-based quadratic indices are calculated using ESk as operators of quadratic transformations. The study of six representative physicochemical properties of octane isomers was used to compare the ability of both series of MDs to produce significant quantitative structure-property relationship (QSPR) models. Moreover, the general performance of the new MDs in this QSPR study has been evaluated with respect to other 2D/3D well-known sets of indices and the obtained results shown a quite satisfactory behavior of the present method. The novel bond-level MDs were also used for the description and prediction of the boiling point of 28 alkyl-alcohols and to the modeling of the specific rate constant (log k) of 34 derivatives of 2-furylethylenes. These models were statistically significant and showed very good stability to data variation in leave-one-out (LOO) cross-validation experiment. The comparison with other approaches (edge- and vertices-based connectivity indices, total and local spectral moments, and quantum chemical descriptors as well as E-state/biomolecular encounter parameters) expose a good behavior of our method in this QSPR studies. The approach described in this report appears to be a very promising structural invariant, useful for QSPR/QSAR studies, similarity/diversity analysis, and computer-aided "rational" molecular (drug) design.