Electrochemical reduction of 1,4-benzoquinone. Interaction with alkylated thymine and adenine nucleobases |
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| Authors: | Magali Salas Mart??n Gómez Felipe J González Barbara Gordillo |
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| Institution: | Departamento de Qu??mica del Centro de Investigación y Estudios Avanzados del I.P.N, Av. Instituto Politécnico Nacional 2508, Apdo. Postal 14-740, C.P. 07360, México D.F., Mexico |
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| Abstract: | The electrochemical reduction of 1,4-benzoquinone (Q) in the presence of 1-octylthymine and 9-octyladenine has been performed in dimethylsulfoxide on glassy carbon electrodes. The electrochemical behaviour shows that the semiquinone (Q![/><sup>?</sup>) and the quinone dianion (Q<sup>2?</sup>) interact with 1-octylthymine (TH) following a mechanism which involves association and protonation reactions. It is demonstrated by cyclic voltammetry and NMR experiments, that the protonated dianion (QH<sup>?</sup>) is stabilised by an excess of TH, alternatively it disproportionates into an association complex of dianion-hydroquinone Q,QH<sub>2</sub>]<sup>2?</sup>. The 1-octylthymine anion (T<sup>?</sup>) produced in the proton transfer reactions activates a homogeneous chain mechanism allowing the consumption of benzoquinone. For the experiments carried out in the presence of 9-octyladenine (AH), it was observed that only a strong hydrogen bonding association takes place between the nucleobase and Q<sup>2?</sup>.</td>
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| Keywords: | Hydrogen bonding 1-Octylthymine 9-Octyladenine 1 4-Benzoquinone reduction |
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