Molecular quantum similarity of enantiomers of amino acids: a case study

In this paper, methodological in nature, molecular quantum similarity is evaluated for enantiomers in the case of molecules showing conformational flexibility, proposing the use of a Boltzmann weighted similarity index. As a case study, the conformers of the enantiomers of the amino acids Alanine and Serine were examined. The second aim is, next to studying global indices, the evaluation of local similarity using our earlier proposed local similarity index based on the Hirshfeld partitioning, in order to further quantify the consequences of Mezey's Holographic Electron Density Theorem in chiral systems.