The mechanism of oxidation of 3-mercaptopropionic acid

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The mechanism of the oxidation of 3-mercaptopropionic acid (3-MPA) by hydrogen peroxide was studied in the acidic pH range. The nucleophilic attack by sulphur on the peroxide bond controls the rate. Extrapolation of the pH dependency suggests that the rate of attack by the deprotonated dianion is hi...

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Detalles Bibliográficos
Autor principal: Forlano, P.
Otros Autores: Olabe, J.A, Magallanes, J.F, Blesa, M.A
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: National Research Council of Canada 1997
Materias:
PH
Acceso en línea:Registro en Scopus
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100 1 |a Forlano, P. 
245 1 4 |a The mechanism of oxidation of 3-mercaptopropionic acid 
260 |b National Research Council of Canada  |c 1997 
270 1 0 |m Blesa, M.A.; Inst. Quim. Fis. Mat., Medio A., Depto. de Quim. Inorgánica, Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: miblesa@cnea.edu.ar 
506 |2 openaire  |e Política editorial 
504 |a Neville, R.G., (1957) J. Am. Chem. Soc., 79, p. 2456 
504 |a Pascal, I., Tarbell, D.S., (1957) J. Amer. Chem. Soc., 79, p. 6015 
504 |a Barton, J.P., Packer, J.E., Sims, R.J., (1973) J. Chem. Soc. Perkin Trans., 2, p. 1547 
504 |a Baiocchi, C., Mentasti, E., Arselli, P., (1983) Transition Met. Chem., 8, p. 40. , London, and refs. therein 
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504 |a Jameson, R.F., Linert, W., Tschinkowitz, A., (1988) J. Chem. Soc. Dalton Trans., p. 2109 
504 |a Deutsch, E., Root, M.J., Nosco, D.L., (1983) Adv. Inorg. Bioinorg. Mech., p. 269 
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504 |a Hoffmann, M.R., (1990) Aquatic Chemical Kinetics, pp. 71-111. , Edited by W. Stumm. Wiley, New York 
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504 |a Birke, R.L., Mazorra, M., (1980) Anal. Chim. Acta., 118, p. 257 
504 |a Kolthoff, I.M., Lingane, J.J., (1952) Polarography, 2, pp. 552-553. , Interscience Publishers, New York 
504 |a Martell, E.A., Smith, R.M., (1974) Critical Stability Constants, 1. , Plenum Press, New York 
504 |a Davis, F.A., Billmers, R.L., (1981) J. Am. Chem. Soc., 103, p. 7016 
504 |a Borghi, E.B., Morando, P.J., Blesa, M.A., (1991) Langmuir, 7, p. 1652 
504 |a Kolthoff, I.M., Barnum, C., (1940) J. Am. Chem. Soc., 62, p. 3061 
504 |a Kolthoff, I.M., Lingane, J.J., (1952) Polarography, 2, pp. 781-791. , Interscience Publishers, New York 
504 |a Mairanovskii, S.G., (1968) Catalytic and Kinetic Waves in Polarography, pp. 228-231. , Plenum Press, New York 
504 |a Laviron, E., Meunier-Prest, R., (1994) J. Electroanal. Chem., 375, p. 79 
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504 |a Feldberg, S.W., (1981) J. Electroanal. Chem., 127, p. 1 
504 |a Marioli, J.M., Magallanes, J.F., Sereno, L., (1991) Bol. Soc. Chil. Quim., 36, p. 157 
520 3 |a The mechanism of the oxidation of 3-mercaptopropionic acid (3-MPA) by hydrogen peroxide was studied in the acidic pH range. The nucleophilic attack by sulphur on the peroxide bond controls the rate. Extrapolation of the pH dependency suggests that the rate of attack by the deprotonated dianion is highest. Traces of Fe(III), at levels below 10-7 mol dm-3, do not catalyze efficiently the process through one-electron mechanisms; at higher concentrations, or on the surface of iron(III) oxides, this type of catalysis becomes important. The electrochemical oxidation of 3-MPA was also studied, using differential pulse polarography and cyclic voltammetry techniques. The mechanism is of the EC2E type, the second electron transfer step corresponding to the oxidation of the disulphide RS-SR. The rate constant for the dimerization of the RS. radicals was 1.8 × 103 mol-1 dm3 s-1; the slowness of this step agrees with the mechanisms observed in the course of one-electron oxidations by metal ions.  |l eng 
593 |a Inst. Quim. Fis. Mat., Medio A., Depto. de Quim. Inorgánica, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
593 |a Unidad de Actividad Química, Comn. Nac. de Ener. Atómica, Avenida del Libertador 8250, 1429 Buenos Aires, Argentina 
690 1 0 |a 3-MERCAPTOPROPIONIC ACID 
690 1 0 |a AUTOOXIDATION 
690 1 0 |a ELECTROCHEMISTRY 
690 1 0 |a KINETICS 
690 1 0 |a CATALYSIS 
690 1 0 |a CHARGE TRANSFER 
690 1 0 |a CYCLIC VOLTAMMETRY 
690 1 0 |a ELECTROCHEMISTRY 
690 1 0 |a ELECTRONS 
690 1 0 |a HYDROGEN PEROXIDE 
690 1 0 |a IRON COMPOUNDS 
690 1 0 |a ORGANIC ACIDS 
690 1 0 |a POLAROGRAPHIC ANALYSIS 
690 1 0 |a REACTION KINETICS 
690 1 0 |a AUTOOXIDATION 
690 1 0 |a DEPROTONATED DIANION 
690 1 0 |a MERCAPTOPROPIONIC ACID 
690 1 0 |a NUCLEOPHILIC ATTACK 
690 1 0 |a SECOND ELECTRON TRANSFER STEP 
690 1 0 |a OXIDATION 
650 1 7 |2 spines  |a PH 
700 1 |a Olabe, J.A. 
700 1 |a Magallanes, J.F. 
700 1 |a Blesa, M.A. 
773 0 |d National Research Council of Canada, 1997  |g v. 75  |h pp. 9-13  |k n. 1  |p Can. J. Chem.  |x 00084042  |w (AR-BaUEN)CENRE-94  |t Canadian Journal of Chemistry 
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856 4 0 |u https://doi.org/10.1139/v97-002  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_00084042_v75_n1_p9_Forlano  |y Handle 
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962 |a info:eu-repo/semantics/article  |a info:ar-repo/semantics/artículo  |b info:eu-repo/semantics/publishedVersion 
999 |c 81087 

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