Effects of bentonite on p-methoxybenzyl acetate: a theoretical model for oligomerization via an electrophilic-substitution mechanism

Molecules. 2011 Feb 21;16(2):1761-75. doi: 10.3390/molecules16021761.

Abstract

Tonsil Actisil FF, a commercial bentonitic clay, promotes the formation of a series of electrophilic-aromatic-substitution products from para-methoxybenzyl acetate in carbon disulfide. The molecules obtained correspond to linear isomeric dimers, trimers, tetramers and a pentamer, according to their spectroscopic data. A clear indication of the title mechanistic pathway for the oligomerization growth was obtained from the analysis of a set of computational-chemistry calculations using the density-functional-theory level B3LYP/6-311++G(d,p). The corresponding conclusions were based on the computed dipole moments, the HOMO/LUMO distributions, and a natural-populations analysis of the studied molecules.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry*
  • Bentonite / chemistry*
  • Computer Simulation
  • Models, Theoretical*
  • Molecular Structure

Substances

  • Acetates
  • Bentonite