Abstract
In the current study, effects of thermodynamic on the reaction mechanisms of the electrochemical oxidation of hydroquinone and catechol in the presence of various nucleophiles have been investigated both experimentally and theoretically, using cyclic voltammetry, controlled-potential coulometry, and density functional theory. The theoretical results were calculated at DFT (B3LYP) level of theory and 6-311+G(p,d) basis set. Calculated ΔG tot of the oxidation of the intermediates and products indicated that thermodynamic is one of the important parameters on the reaction mechanisms. The results of this work show that depending on the ΔG tot of electrochemical oxidation, the intermediates which are produced on the surface of electrode will participate in the electrochemical or chemical following reactions.
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Du J, Ma L, Shan D, Fan Y, Zhang L, Wang L, Lu X (2014) J Electroanal Chem 38:722
Wang J, Park JN, Wei XY, Lee CW (2003) Chem Commun 628
Zhao DM, Zhang XH, Feng LJ, Jia L, Wang SF (2009) Colloids Surf B Biointerfaces 74:317
Zhao GH, Li MF, Hu ZH, Li HX, Cao TC (2006) J Mol Catal A Chem 255:86
Gaskell M, McLuckie KI, Farmer PB (2004) Mutat Res Fundam Mol Mech Mutagen 554:387
Hirakawa K, Oikawa S, Hiraku Y, Hirosawa I, Kawanishi S (2002) Chem Res Toxicol 15:76
Blum RH, Carter SK (1974) Ann Int Med 80:249
Wang X, Wu M, Li H, Wang Q, He P, Fang Y (2014) Sens Actuators B 192:452
Lai T, Cai W, Dai W, Ye J (2014) Electrochim Acta 48:138
Tang W, Zhang M, Li W, Zeng X (2014) Talanta 127:262
Yin H, Zhang Q, Zhou Y, Ma Q, Liu T, Zhu L, Ai S (2011) Electrochim Acta 56:2748
Ramsden CA, Riley PA (2014) Bioorg Med Chem Lett 24:2463
Han HS, You JM, Seol H, Jeong H, Jeon S (2014) Sens Actuators B 194:460
Nematollahi D, Momeni S, Khazalpour S (2014) Electrochim Acta 147:310
Nourmohammadi F, Golabi SM, Saadnia A (2002) J Electroanal Chem 529:12
Nematollahi D, Tammari E, Esmaili R (2008) J Electroanal Chem 621:113
Nematollahi D, Dadpou B (2011) Monatsh Chem 142:1235
Nematollahi D, Khoshsafar H (2009) Tetrahedron 65:4742
Nematollahi D, Tammari E (2005) J Org Chem 70:7769
Nematollahi D, Azizian J, Sargordani-Arani M, Hesari M, Jameh-Bozorgi S, Alizadeh A, Fotohi L, Mirza B (2008) Chem Pharm Bull 56:1562
Nematollahi D, Bamzadeh M, Shayani-Jam H (2010) Chem Pharm Bull 58:23
Nematollahi D, Hesari M (2005) J Electroanal Chem 577:197
Nematollahi D, Tammari E, Sharifi S, Kazemi M (2004) Electrochim Acta 49:591
Nematollahi D, Dehdashtian S (2008) Tetrahedron Lett 49:645
Beiginejad H, Nematollahi D, Bayat M, Varmaghani F, Nazaripour A (2013) J Electrochem Soc 160:H693
Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven JT, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian 03, revision B.04. Gaussian, Inc, Pittsburgh
HyperChem (1997) Release 5.02. Hypercube, Inc., Gainesville, FL
Barone V, Cossi M (1998) J Phys Chem A 102:1995
Levin IN (1988) Physical chemistry, 3rd edn. McGraw-Hill, New York, Chapter 22
Gilson MK, Honig BH (1988) Proteins 4:7
Davis AP, Fry AJ (2010) J Phys Chem A 114:12299
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Beiginejad, H., Nematollahi, D. Thermodynamic and electrochemical study of some dihydroxybenzenes in the presence of different nucleophiles. Monatsh Chem 147, 329–339 (2016). https://doi.org/10.1007/s00706-015-1523-7
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DOI: https://doi.org/10.1007/s00706-015-1523-7