Quantitative relationships for the prediction of the vapor pressure of some hydrocarbons from the van der Waals molecular surface

Abstract

A quantitative structure - property relationship (QSPR) modeling of vapor pressure at 298.15 K, expressed as log (VP / Pa) was performed for a series of 84 hydrocarbons (63 alkanes and 21 cycloalkanes) using the van der Waals (vdW) surface area, SW/Å2, calculated by the Monte Carlo method, as the molecular descriptor. The QSPR model developed from the subset of 63 alkanes (C1-C16), deemed as the training set, was successfully used for the prediction of the log (VP / Pa) values of the 21 cycloalkanes, which was the external prediction (test) subset. A QSPR model was also developed for a series composed of all 84 hydrocarbons. Both QSPR models were statistically tested for their ability to fit the data and for prediction. The results showed that the vdW molecular surface used as molecular descriptor (MD) explains the variance of the majority of the log (VP / Pa) values in this series of 84 hydrocarbons. This MD describes very well the intermolecular forces that hold neutral molecules together. The clear physical meaning of the molecular surface values, SW/Å2, could explain the success of the QSPR models obtained with a single structural molecular descriptor.

Keywords

• MD - molecular descriptor
• van der Waals molecular surface
• Monte Carlo method
• QSPR