关键词: 手性拓扑指数, 保留指数, 羟基酸, 氨基酸, 定量关系

Based on topological chemical theory, as well as the bonding atomic structural features and the local chemical microenvironment, we introduced two new chiral topological indices w₁, w₂, with the space distance between atoms using density functional theory (DFT) at the B3LYP/6-31＋G(d) level instead of the traditional topographic distance in two-dimensional topographic distance matrix. In the paper, we also colored all atoms in molecular graph with equilibrium electro-negativity based on distance matrix and branch vertex of atoms in a molecule, and corrected the distance matrix by chiral factors. Quantitative structure-retention relationship (QSRR) was systematically made on relationship between the retention indinces R_M from a chiral thin-layer chromatogram for 18 chiral organic acids (8 hydroxyl acids and 10 amino acids) and the chiral topological index w₁, w₂ by partial least regression (PLS). The calculated results by the model indicate that the average relative deviations between calculated values and experimental data of retention indinces R_M of chiral compounds are among the experimental deviations. To validate the estimation stability for internal samples and the predictive capability for external samples of resulting models, leave-one-out (LOO) cross validation (CV) and external validation were performed. And the results shows that the models all have good stability and predictability.

Key words: chiral topological indices, retention indices, hydroxyl acid, amino acid, quantitative relationship