Molecular size and molecular structure: Discriminating their changes upon chemical reactions in terms of information...

Structural descriptors take the central place in the digitalization of chemical reactions. Information entropy is one of such descriptors that has been a seminal for numerous derivative indices. Previously, we have studied the rules of calculating information entropies of molecular ensembles based on the corresponding values of constituting molecules and found that the complexity of the ensemble has the contributions from the molecular structure and the size of the molecules. Considering chemical reaction as the conversion of one molecular ensemble to another allows calculating the change in information entropy as well as its components associated with molecular-structure and molecular-size changes. We demonstrate that both total information entropy change and its contributions are characteristic for the selected classes of chemical reactions and exemplify this approach with the cycloaddition and exchange reactions widespread in organic chemistry.