Semi-empirical topological index: Development of QSPR/QSRR and optimization for alkylbenzenes

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• 作者：Ledilege Cucco Porto ; É ; rica Silva Souza ; Berenice da Silva Junkes ; Rosendo Augusto Yunes ; Vilma Edite Fonseca Heinzen
• 关键词：Gas chromatographic retention indices ; Topological indices ; Alkylbenzenes ; Quantitative structure– ; retention relationships ; Semi-empirical topological index
• 刊名：Talanta
• 出版年：2008
• 期刊代码：106_00399140
• 类别：ch
• 出版时间：15 July 2008
• 卷：76
• 期：2
• 页码：407-412
• 文件大小：292 K

摘要

The semi-empirical topological index, I_ET, was developed and optimized to describe the chromatographic retention of alkylbenzenes on the squalane stationary phase. The simple linear regression between the chromatographic retention and the proposed index, for 122 alkylbenzenes studied, is of good quality (determination coefficient, r² = 0.9996, standard deviation, S.D. = 5.5, and leave-one-out cross-validation correlation coefficient, ). The predictive ability of I_ET was also verified for stationary phases with two different polarities (SE-30 and Carbowax 20 M), and good results were obtained, especially for the stationary phase with low polarity, showing that the specific molecular interactions occur on highly polar phases. The I_ET was applied to construct quantitative structure–property relationship (QSPR) models for representative properties such as boiling point, Bp(°C), octanol/water partition coefficient, log P, van der Waals volume (V_W) and molar refractivity (R_M). Satisfactory quality QSPR models were obtained with Bp, V_W and R_M showing that the molecular size and dispersive forces are dominating factors with respect to the chromatographic retention.