Phenol And Para-Substituted Phenols Electrochemical Oxidation Pathways

The electrochemical behaviour of phenol, catechol, hydroquinone, resorcinol, dopamine, and para-substituted phenolic compounds, 4-ethylphenol, tyrosine, and tyramine, was studied over a wide pH range using a glassy carbon electrode. The oxidation of phenol is pH dependent and irreversible, occurring in one step, and followed by hydrolyse in ortho- and para-positions, leading to two oxidation products, catechol and hydroquinone. The oxidation of phenol oxidation products, ortho-phenol and para-phenol, is reversible and pH dependent. The oxidation potential of para-substituted phenols varies slightly due to their substituent group in position C4, and occurs in one oxidation step corresponding to the oxidation of phenol. The oxidation products of this group of para-substituted phenols are reversibly oxidised and adsorb on the electrode surface.

[1]  R. McCreery,et al.  Control of Electron Transfer Kinetics at Glassy Carbon Electrodes by Specific Surface Modification , 1996 .

[2]  M. Panizza,et al.  Electrochemical oxidation of phenol at boron-doped diamond electrode. Application to electro-organic synthesis and wastewater treatment. , 2001, Annali di chimica.

[3]  L. Barclay,et al.  Media Effects on Antioxidant Activities of Phenols and Catechols , 1999 .

[4]  I. Karafyllis,et al.  Anodic oxidation of phenol on Ti/IrO2 electrode: Experimental studies , 2010 .

[5]  V. De Feo,et al.  Chemistry, Antioxidant, Antibacterial and Antifungal Activities of Volatile Oils and their Components , 2009, Natural product communications.

[6]  D. Leibfritz,et al.  Free radicals and antioxidants in normal physiological functions and human disease. , 2007, The international journal of biochemistry & cell biology.

[7]  Nino Russo,et al.  Antioxidant Properties of Phenolic Compounds: H-Atom versus Electron Transfer Mechanism , 2004 .

[8]  A. M. Brett,et al.  Catechin electrochemical oxidation mechanisms , 2004 .

[9]  J. L. Stringer,et al.  Characterization of chemical ingredients and anticonvulsant activity of American skullcap (Scutellaria lateriflora). , 2009, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[10]  Francesco Castelli,et al.  Interaction of four monoterpenes contained in essential oils with model membranes: implications for their antibacterial activity. , 2007, Journal of agricultural and food chemistry.

[11]  M. C. M. Nadra,et al.  Antibacterial effect of phenolic compounds from different wines , 2007 .

[12]  D. Andreescu,et al.  A new electrocatalytic mechanism for the oxidation of phenols at platinum electrodes , 2003 .

[13]  J. R.,et al.  Chemistry , 1929, Nature.

[14]  J. Boudenne,et al.  Electrochemical oxidation of aqueous phenol at a carbon black slurry electrode , 1996 .

[15]  B. Malfoy,et al.  Electrochemical investigations of amino acids at solid electrodes: Part II. Amino acids containing no sulfur atoms: Tryptophan, tyrosine, histidine and derivatives , 1980 .

[16]  E. Denisov,et al.  Oxidation and Antioxidants in Organic Chemistry and Biology , 2005 .

[17]  B. Malfoy,et al.  The electrochemical oxidation of three proteins: RNAase A, bovine serum albumin and concanavalin A at solid electrodes* , 1980 .

[18]  B. Malfoy,et al.  Electrochemical investigations of amino acids at solid electrodes: Part I. Sulfur components: Cystine, cysteine, methionine , 1980 .

[19]  M. Šeruga,et al.  Square-wave and cyclic voltammetry of epicatechin gallate on glassy carbon electrode , 2009 .

[20]  O. Aruoma,et al.  Phenolics as potential antioxidant therapeutic agents: mechanism and actions. , 2005, Mutation research.

[21]  Akira Fujishima,et al.  Tyrosinase-modified boron-doped diamond electrodes for the determination of phenol derivatives , 2002 .

[22]  S. Shahrokhian,et al.  Electrochemical oxidation of dopamine in the presence of sulfhydryl compounds: Application to the square-wave voltammetric detection of penicillamine and cysteine , 2006 .

[23]  V. Brabec.  Electrochemical oxidation of nucleic acids and proteins at graphite electrode. Qualitative aspects , 1980 .

[24]  J. Pereira,et al.  Phenolics: From Chemistry to Biology , 2009, Molecules.

[25]  A. M. Brett,et al.  Redox Behavior of Anthocyanins Present in Vitis vinifera L. , 2007 .

[26]  S. Ercişli,et al.  Total phenolic content, antioxidant and antimicrobial activities of some medicinal plants. , 2009, Pakistan journal of pharmaceutical sciences.

[27]  J. Calzón,et al.  Square-wave voltammetry of the o-catechol–Ge(IV) catalytic system after adsorptive preconcentration at a hanging mercury drop electrode , 2001 .

[28]  G. G. Stokes.  "J." , 1890, The New Yale Book of Quotations.

[29]  John B. Shoven,et al.  I , Edinburgh Medical and Surgical Journal.

[30]  P. Cañizares,et al.  Electrochemical oxidation of hydroquinone, resorcinol, and catechol on boron-doped diamond anodes. , 2005, Environmental science & technology.