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Molecules 2011, 16(2), 1761-1775; doi:10.3390/molecules16021761
Article

Effects of Bentonite on p-Methoxybenzyl Acetate: A Theoretical Model for Oligomerization via an Electrophilic-Substitution Mechanism

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Received: 29 November 2010 / Revised: 14 February 2011 / Accepted: 15 February 2011 / Published: 21 February 2011
(This article belongs to the Section Organic Synthesis)
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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.
Keywords: bentonitic clay; para-methoxybenzyl acetate; oligomerization; electrophilic aromatic substitution; DFT calculations bentonitic clay; para-methoxybenzyl acetate; oligomerization; electrophilic aromatic substitution; DFT calculations
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Salmón, M.; Miranda, R.; Nicolás-Vázquez, I.; Vargas-Rodriguez, Y.M.; Cruz-Borbolla, J.; Medrano, M.I.; Morales-Serna, J.A. Effects of Bentonite on p-Methoxybenzyl Acetate: A Theoretical Model for Oligomerization via an Electrophilic-Substitution Mechanism. Molecules 2011, 16, 1761-1775.

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