4.7 Article

Chemical oxidative polymerization of benzocaine

Journal

REACTIVE & FUNCTIONAL POLYMERS
Volume 71, Issue 7, Pages 704-712

Publisher

ELSEVIER SCIENCE BV
DOI: 10.1016/j.reactfunctpolym.2011.03.013

Keywords

Benzocaine; Electro-active oligomer; Oxidative polymerization; Functionalized oligoaniline

Funding

  1. Ministry of Science and Technological Development of Serbia [172035, 172043]
  2. Czech Grant Agency [203/08/0686]

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Novel electroactive paramagnetic ortho-coupled aniline oligomers functionalized with ethyl ester groups were synthesized by the oxidation of the 4-carbethoxyaniline, well known anesthetic benzocaine, with ammonium peroxydisulfate in an acidic aqueous medium at room temperature. Oligobenzocaines were characterized by elemental analysis, gel-permeation chromatography, conductivity measurements, FTIR, Raman and EPR spectroscopies, and scanning electron microscopy. Theoretical study of the mechanism of benzocaine oxidation has been based on the AM1 and RM1 semi-empirical quantum chemical computations of the heat of formation and ionization energy of the benzocaine, protonated benzocaine, generated reactive species and reaction intermediates, taking into account influence of pH and solvation effects. Electroactivity of the oligobenzocaines was studied by the cyclic voltammetry. (C) 2011 Elsevier Ltd. All rights reserved.

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