A Molecular Modeling Study on the Isopropylation of Naphthalene with Propene Using an Amorphous Silica–Alumina Catalyst in the Kinetic and Thermodynamic Regime

The aim of this publication is to compare computationally obtained distributions of mono-, di-, tri-, and tetra-isopropylnaphthalenes with experimentally obtained ones in the kinetic regime and the thermodynamic regime. Several DFT codes and MP2 were applied in the kinetic regime. Based on computationally obtained activation enthalpies, a simple and an extended kinetic model were developed to yield distributions of isopropylated naphthalenes and the partition of diisopropylnaphhalenes. The simple kinetic model was used to select a suitable model catalytic system and a computational code for the extended model. B3LYP/6–31G* and B3PW91/6–31G* performed well, while ωB97X-D/6–31G* and MP2/6–31G* did not. It was found that computational results obtained with an extended kinetic model applying B3LYP/6–31G* very closely resemble the experimental distribution of mono-, di-, tri-, and tetra-isopropylnaphthalenes, including the internal partition of the DIPNs, both in the kinetic regime and the thermodynamic regime.