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

1 Instituto de Química de la Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria Coyoacán 04510, México, D.F., Mexico 2 Sección de Química Inorgánica, Fisicoquímica y Química Orgánica, Departamento de Ciencias Químicas, Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Cuatitlán Izcalli, 54740, Estado de México, Mexico 3 Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, Unidad Universitaria, Km 4.5 Carretera Pachuca-Tulancingo, Mineral de Reforma, 42184, Hidalgo, Mexico
* Authors to whom correspondence should be addressed.
Received: 29 November 2010; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

Salmón M, Miranda R, Nicolás-Vázquez I, Vargas-Rodriguez YM, Cruz-Borbolla J, Medrano MI, Morales-Serna JA. Effects of Bentonite on p-Methoxybenzyl Acetate: A Theoretical Model for Oligomerization via an Electrophilic-Substitution Mechanism. Molecules. 2011; 16(2):1761-1775.

Chicago/Turabian Style

Salmón, Manuel; Miranda, Rene; Nicolás-Vázquez, Ines; Vargas-Rodriguez, Yolanda Marina; Cruz-Borbolla, Julian; Medrano, María Isabel; Morales-Serna, José Antonio. 2011. "Effects of Bentonite on p-Methoxybenzyl Acetate: A Theoretical Model for Oligomerization via an Electrophilic-Substitution Mechanism." Molecules 16, no. 2: 1761-1775.

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