Molecular modeling study on the possible polymers formed during the electropolymerization of 3-hydroxyphenylacetic acid

[Display omitted] ► DFT study on the electropolymerization of 3-hydroxy phenylacetic acid. ► Proposed reaction mechanism, based on theoretical and experimental evidence. ► Conformational analysis of oligomeric models. ► Calculation of oligomers IR spectra for validation of the mechanistic proposal....

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Bibliographic Details
Published in:Journal of molecular graphics & modelling 2012-04, Vol.34, p.18-27
Main Authors: Ferreira, Deusmaque Carneiro, Machado, Antonio Eduardo da Hora, Tiago, Fernanda de Souza, Madurro, João Marcos, Madurro, Ana Graci Brito, Abrahão, Odonírio
Format: Article
Language:English
Subjects:
Computer Simulation
Conductive polymer
DFT
Electrochemical biosensors
Electrochemistry
Electrons
Membranes, Artificial
Models, Molecular
Molecular Conformation
Monte Carlo conformational analysis
Phenylacetates - chemistry
Polymer structure
Polymerization
Polymers - chemistry
Quantum Theory
Reaction mechanism
RM1
Spectroscopy, Fourier Transform Infrared
Surface Properties
Thermodynamics
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Summary:[Display omitted] ► DFT study on the electropolymerization of 3-hydroxy phenylacetic acid. ► Proposed reaction mechanism, based on theoretical and experimental evidence. ► Conformational analysis of oligomeric models. ► Calculation of oligomers IR spectra for validation of the mechanistic proposal. The compound 3-hydroxyphenylacetic acid (3-HPA) has been used as a monomer in the synthesis of polymeric films by electropolymerization; these films serve as supports for the immobilization of biomolecules in electrochemical biosensors. To assist in the elucidation of the mechanism of 3-HPA electropolymerization, a systematic quantum mechanical study was conducted. In addition to the monomer, all possible intermediates and the probable oligomers formed during the electropolymerization were investigated using a density functional theory (DFT) method combined with a previous conformational analysis performed with the aid of the RM1 semi-empirical method or a Monte Carlo conformational analysis with the force field OPLS-2005. From the data analysis combined with the experimental results, a mechanism was proposed for the main route of formation of the polymeric films. The mechanism involves the formation of polyethers from the coupling of phenoxide radicals and radicals based on the aromatic ring.
ISSN:1093-3263
1873-4243
DOI:10.1016/j.jmgm.2012.01.001