Mechanism of oxidation of 1-benzyl-1,4-dihydronicotinamide by the biologically active p-benzoquinone derivative, avarone, in a cationic micellar medium. An electrochemical approach
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1991
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The electrochemical reduction of avarone (Q), an antitumor sesquiterpenoid quinone, was investigated at various pH in aqueous ethanol containing a cationic surfactant, cetyltrimethylammonium bromide (CTAB) by cyclic and rotating disc electrode voltammetry, using a glassy carbon electrode. Comparison of the electrochemical reduction of Q in presence of CTAB with the same process in a homogeneous water + ethanol solution shows an anodic shift of the reduction potential in the presence of CTAB; at pH gt 9.5 and in presence of CTAB, two well-defined reduction peaks are observed, thus confirming one-electron reduction of Q, whereby the intermediate radical-anion is stabilized by the cationic micellar medium. The electrochemical oxidation of BNAH was investigated by cyclic voltammetry, and the anodic shift of the peak potential in presence of CTAB was observed. From the electrochemical behaviour of Q and BNAH, and the kinetics of the oxidation of BNAH with Q, it is suggested that the react...ion takes place in two successive one-electron transfer steps. The application of the Marcus theory gives additional proof that, in this case, the first electron transfer is the rate determining step. © 1991.
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Bioelectrochemistry and Bioenergetics, 1991, 26, 3, 457-468Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Davidović, A. AU - Tabaković, I. AU - Sladić, Dušan AU - Dogović, N. AU - Gašic, M.J. PY - 1991 UR - https://cherry.chem.bg.ac.rs/handle/123456789/24 AB - The electrochemical reduction of avarone (Q), an antitumor sesquiterpenoid quinone, was investigated at various pH in aqueous ethanol containing a cationic surfactant, cetyltrimethylammonium bromide (CTAB) by cyclic and rotating disc electrode voltammetry, using a glassy carbon electrode. Comparison of the electrochemical reduction of Q in presence of CTAB with the same process in a homogeneous water + ethanol solution shows an anodic shift of the reduction potential in the presence of CTAB; at pH gt 9.5 and in presence of CTAB, two well-defined reduction peaks are observed, thus confirming one-electron reduction of Q, whereby the intermediate radical-anion is stabilized by the cationic micellar medium. The electrochemical oxidation of BNAH was investigated by cyclic voltammetry, and the anodic shift of the peak potential in presence of CTAB was observed. From the electrochemical behaviour of Q and BNAH, and the kinetics of the oxidation of BNAH with Q, it is suggested that the reaction takes place in two successive one-electron transfer steps. The application of the Marcus theory gives additional proof that, in this case, the first electron transfer is the rate determining step. © 1991. T2 - Bioelectrochemistry and Bioenergetics T1 - Mechanism of oxidation of 1-benzyl-1,4-dihydronicotinamide by the biologically active p-benzoquinone derivative, avarone, in a cationic micellar medium. An electrochemical approach VL - 26 IS - 3 SP - 457 EP - 468 DO - 10.1016/0302-4598(91)85007-O ER -
@article{ author = "Davidović, A. and Tabaković, I. and Sladić, Dušan and Dogović, N. and Gašic, M.J.", year = "1991", abstract = "The electrochemical reduction of avarone (Q), an antitumor sesquiterpenoid quinone, was investigated at various pH in aqueous ethanol containing a cationic surfactant, cetyltrimethylammonium bromide (CTAB) by cyclic and rotating disc electrode voltammetry, using a glassy carbon electrode. Comparison of the electrochemical reduction of Q in presence of CTAB with the same process in a homogeneous water + ethanol solution shows an anodic shift of the reduction potential in the presence of CTAB; at pH gt 9.5 and in presence of CTAB, two well-defined reduction peaks are observed, thus confirming one-electron reduction of Q, whereby the intermediate radical-anion is stabilized by the cationic micellar medium. The electrochemical oxidation of BNAH was investigated by cyclic voltammetry, and the anodic shift of the peak potential in presence of CTAB was observed. From the electrochemical behaviour of Q and BNAH, and the kinetics of the oxidation of BNAH with Q, it is suggested that the reaction takes place in two successive one-electron transfer steps. The application of the Marcus theory gives additional proof that, in this case, the first electron transfer is the rate determining step. © 1991.", journal = "Bioelectrochemistry and Bioenergetics", title = "Mechanism of oxidation of 1-benzyl-1,4-dihydronicotinamide by the biologically active p-benzoquinone derivative, avarone, in a cationic micellar medium. An electrochemical approach", volume = "26", number = "3", pages = "457-468", doi = "10.1016/0302-4598(91)85007-O" }
Davidović, A., Tabaković, I., Sladić, D., Dogović, N.,& Gašic, M.J.. (1991). Mechanism of oxidation of 1-benzyl-1,4-dihydronicotinamide by the biologically active p-benzoquinone derivative, avarone, in a cationic micellar medium. An electrochemical approach. in Bioelectrochemistry and Bioenergetics, 26(3), 457-468. https://doi.org/10.1016/0302-4598(91)85007-O
Davidović A, Tabaković I, Sladić D, Dogović N, Gašic M. Mechanism of oxidation of 1-benzyl-1,4-dihydronicotinamide by the biologically active p-benzoquinone derivative, avarone, in a cationic micellar medium. An electrochemical approach. in Bioelectrochemistry and Bioenergetics. 1991;26(3):457-468. doi:10.1016/0302-4598(91)85007-O .
Davidović, A., Tabaković, I., Sladić, Dušan, Dogović, N., Gašic, M.J., "Mechanism of oxidation of 1-benzyl-1,4-dihydronicotinamide by the biologically active p-benzoquinone derivative, avarone, in a cationic micellar medium. An electrochemical approach" in Bioelectrochemistry and Bioenergetics, 26, no. 3 (1991):457-468, https://doi.org/10.1016/0302-4598(91)85007-O . .