Qspr models for the molar refraction, polarizability and refractive index of aliphatic carboxylic acids using the zep topological index

Abstract

The molar refraction, polarizability, and refractive index for a series of monocarboxylic, dicarboxylic, and unsaturated monocarboxylic acids, having a symmetric or asymmetric structure, were investigated by the application of quantitative structure property relationship (QSPR) technique. We used a linear regression method and a single molecular descriptor, the ZEP topological index, calculated in a simple manner, with the help of weighted electronic distances, and also calculated on the basis of the chemical structure of the molecules. The high-quality performance and predictive ability of the QSPR models obtained were validated by means of specific validation techniques: y-randomization test, the leave-one-out cross validation procedure, and external validation. The investigated properties are well modeled (with r2 > 0.99) by the ZEP index, using the regression analysis as a statistical tool for developing reliable QSPR models. Our approach provides an alternative technique to the existing additive methods for predicting the molar refraction and polarizability of carboxylic acids, which is essentially based on the summation of atom and/or functional group contributions or bond contributions, and of some correction increments.