拓扑-量子指数醛酮气相色谱保留指数及沸点的定量构效关系

通过对醛酮化合物分子结构特征及其气相色谱保留指数(RI)和沸点与分子结构间关系的研究,提出了分子极化效应指数(MPEI)、奇偶指数(OEI)、立体效应指数(SVij)、顶点度-距离指数(VDI)及键连接矩阵特征根(∑X1CH)等拓扑-量子结构参数,用多元线性回归(MLR)方法获得了醛酮类化合物的沸点及其在不同极性色谱柱上的气相色谱保留指数与这些拓扑-量子指数间良好的定量结构-性质相关(QSPR)模型,相关系数均大于0.99。5个分子结构参数具有明确的物理化学意义且易于计算和运用。与文献研究的比较结果表明:由上述分子结构参数得出的模型方程适用于各类醛酮化合物的气相色谱保留指数及沸点的预测且具有较好的稳定性和准确性。     

Development of a quantitative structure--property relationship model for estimating normal boiling points of small multifunctional organic molecules

Computer-assisted quantitative structure-property relationship techniques are applied in the development of a robust and accurate model of normal boiling points (boiling at 760 mmHg) for a very diverse set of 268 small organic molecules. Most of the molecules included in this study contain two or more functional groups. The final model yields a tight fit to the training set data (R2 = 0.963), with a fit error of 6.5%. More importantly, the model is also shown to perform well in external prediction. The mean prediction error for boiling points for a 78-member external test set was 12.3 degrees C, or 8.3%. A detailed analysis of the small number of compounds that were either outliers or not well predicted illustrates areas for potential improvement of the methodology used.