Topological model to quantify the global reactivity indexes as local in Diels–Alder reactions, using density function theory (DFT) and local quantum similarity (LQS)

Abstract

In this study is presented a Topological model for quantify the global reactivity indexes as local in Diels–Alder Reactions. Using conceptual density functional theory (DFT) and molecular quantum similarity (MQS), by means of six local similarity indexes: Overlap, Overlap-Interaction, Coulomb, Coulomb-Interaction, with their respective Euclidean distances. Using the Topo-Geometrical Superposition Approach (Topo-Geometrical superposition Algorithm) as method of alignment. This allowed us to obtain good results in local similarity indexes. This methodology proved to be an appropriate technique for the intended purpose, found that values of local electrophilic and hardness calculated are in agreement with the theoretical and experimental mechanism of cycloaddition considered here in this work. In addition chemical potential of Overlap and Coulomb proposed reproduce the trend of the values of the Fukui function (F−) of atom C6 in the dihydrofuran derivatives present in the cycloaddition reaction considered. Taking into account that the C6 carbon atom is responsible for the preferred stereochemistry, this evidence allowed us propose this methodology as alternative way to determining of local reactivity indexes using MQS based on the Hirshfeld partitioning. In addition in this contribution was postulated a new perspectives in the chemical reactivity field such as chemical potential, hardness and electrophilicity relative, alternatives to the traditional (chemical potential, hardness and electrophilicity) proposed in the conceptual DFT which allowed us to relate the local reactivity indexes proposed with the global considering that the pursuit of local descriptors of reactivity supported on ideas of MQS in Cycloaddition Reactions.