NDLI: Electrochemical characterization of hydroquinone derivatives with different substituents in acetonitrile

Content Provider	Royal Society of Chemistry (RSC)
Author	Salazar, Ricardo Vidal, Jorge Martínez-Cifuentes, Maximiliano Ramírez-Rodríguez, Oney Araya-Maturana, Ramiro
Copyright Year	2015
Abstract	The effect of carbonyl groups in the ortho position with respect to a hydroxyl group on the electrochemical oxidation of hydroquinones in acetonitrile is studied. The electrochemical response of hydroquinone on a glassy carbon electrode in 0.1 M tetrabutylammonium perchlorate was investigated in detail by voltammetry and coulometry. From these experiments, the oxidation potential was shifted to more positive values with respect to hydroquinone due to the presence of electron withdrawing groups bonded to the aromatic ring. For all compounds a diffusional behavior was observed, and the diffusion coefficient (D) of substituted hydroquinones was calculated showing higher values than found for unsubstituted hydroquinone. Theoretical calculations were carried out to gain insights into the intramolecular hydrogen bond present in these molecules affecting their electrochemical behavior. Relevant theoretical data are optimized geometrical parameters, HOMO energy, condensed radical Fukui functions (f°), natural charges, Wiberg bond orders (WBO), stabilization energies caused by electron transfer, and hyperconjugation stabilization energies from the NBO analysis. In most cases, the calculations show good agreement with experimental 1H-NMR data and support the electrochemical results.
Starting Page	1237
Ending Page	1246
Page Count	10
File Format	HTM / HTML PDF
ISSN	11440546
Volume Number	39
Issue Number	2
Journal	New Journal of Chemistry
DOI	10.1039/c4nj01657b
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Wiberg Perchlorate Electrode HOMO\/LUMO Tetra-n-butylammonium bromide Chemical bond World Boxing Organization Hyperconjugation Voltammetry Carbon Hydroquinone Hydroxy group Acetonitrile Electrochemistry NBO Carbonyl group Diffusion Coulometry Hydrogen bond
Content Type	Text
Resource Type	Article
Subject	Chemistry Materials Chemistry Catalysis

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