Acta Chimica Sinica ›› 2011, Vol. 69 ›› Issue (03): 305-310. Previous Articles     Next Articles

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  1. (1 南华大学化学化工学院 衡阳 421001)
    (2南华大学公共卫生学院 衡阳 421001)
    (3图卢兹第三大学量子化学与物理实验室 法国图卢兹 31077)
    (4 湖南大学化学生物传感与计量学国家重点实验室 长沙 410082)
  • 收稿日期:2010-08-15 修回日期:2010-09-21 出版日期:2011-02-14 发布日期:2010-10-11
  • 通讯作者: 彭国文
  • 基金资助:


Quantum Topological Method Studies on QSRR for Chiral Organic Compounds

Peng Guowen*,1 Xiao Fangzhu#,2 Nie Changming1,3 Liao Lifu1 Yang Shengyuan2,4   

  1. (1 School of Chemistry and Chemical Engineering, University South China, Hengyang 421001)
    (2 School of Public Health, University South China, Hengyang 421001)
    (3 Laboratory of Quantum Chemistry and Physics, University of Paul Sabatier (Toulouse-III), Toulouse 31077, France)
    (4 State Key Laboratory of Chemo-Biosensing and Chemometrics, Hunan University, Changsha 410082)
  • Received:2010-08-15 Revised:2010-09-21 Online:2011-02-14 Published:2010-10-11
  • Contact: PENG GUO-WEN

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 RM 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 RM 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

CLC Number: