Acta Phys. -Chim. Sin. ›› 2015, Vol. 31 ›› Issue (1): 73-82.doi: 10.3866/PKU.WHXB201410281

• THEORETICAL AND COMPUTATIONAL CHEMISTRY • Previous Articles     Next Articles

Predicting Retention and Separation Factors of Chiral Diarylmethane Derivates by QSPR Models

HU Gui-Xiang1, LUO Cheng-Cai1, PAN Shan-Fei2, JIANG Yong-Jun1, ZOU Jian-Wei1   

  1. 1. School of Biotechnology and Chemical Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, Zhejiang Province, P. R. China;
    2. Department of Chemistry, Zhejiang University, Hangzhou 310028, P. R. China
  • Received:2014-08-16 Revised:2014-10-27 Published:2014-12-25
  • Contact: HU Gui-Xiang E-mail:hugx@nit.zju.edu.cn
  • Supported by:

    The project was supported by the National Natural Science Foundation of China (21002088, 21272211) and Programof Science and Technology of Ningbo, China (2013D1003).

Abstract:

Quantitative structure-property relationship (QSPR) studies on retention and separation factors of chiral compounds play a key role in predicting the retention and separation factors even the elution order of enantiomers. Chiral diarylmethane derivates were selected for computing molecular structural descriptors using VolSurf program. Models were built between the descriptors and retention as well as separation factors. The robustness of the model with respect to separation factors was assessed by external validation through the test set, leave-many-out cross-validation and Y-randomization test. The results were satisfactory. Analysis on the variables shows that the molecular globularity, hydrophilic regions at median energy levels, hydrophilic-lipophilic balance, amphiphilic moment, suitable hydrogen bond donors and acceptors are beneficial to the retention of enantiomers on the chiral stationary phase. Large differences of the hydrophilic regions at high energy levels, hydrophobic regions at lowenergy levels, amphiphilic moment, suitable hydrogen bond donors and acceptors, and anion regions between enantiomers are advantageous to the separation of enantiomers on the chiral stationary phase. These models allowthe prediction of retention and separation factors, especially the elution order of enantiomers.

Key words: Chirality, Molecular modeling, VolSurf, Diarylmethane, Partial least squares

MSC2000: 

  • O641