Electrochemical reduction of thymine in dimethyl sulfoxide autoprotonation of the radical anion and reduced free radical
dc.contributor.author | Cummings, Timothy E. | en_US |
dc.contributor.author | Elving, Philip Juliber | en_US |
dc.date.accessioned | 2006-04-07T17:32:31Z | |
dc.date.available | 2006-04-07T17:32:31Z | |
dc.date.issued | 1979-09-25 | en_US |
dc.identifier.citation | Cummings, Timothy E., Elving, Philip J. (1979/09/25)."Electrochemical reduction of thymine in dimethyl sulfoxide autoprotonation of the radical anion and reduced free radical." Journal of Electroanalytical Chemistry 102(2): 237-248. <http://hdl.handle.net/2027.42/23490> | en_US |
dc.identifier.uri | http://www.sciencedirect.com/science/article/B6TGB-45D9NTD-20/2/74ba97cef456e83a9f5e095f88fba712 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/23490 | |
dc.description.abstract | Thymine is reduced in dimethyl sulfoxide (E1/2 of -2.4 V); the decrease in apparent faradaic n from one at inifinite dilution to two-thirds at concentraitons above 2 mM is due to proton transfer by thymine to the initially formed radical anion and the anion formed on reduction of the resulting free radical, which is more easily reduced than the parent compound. The proton transfer, which is more rapid than the radical anion dimerization, deactivates part of the thymine, forming the more difficulty reducible conjugate base. The latter forms insoluble mercury salts, producing up to three oxidation waves (E1/2 between -0.08 and -0.3 V). The free radical reduction, which is not observed for uracil or 2-hydroxypyrimidine, occurs due to steric hindrance by the 5-methyl group toward free radical dimerization, thereby increasing the half-life of the free radical. The effect of added base on the electrochemical behavior is described. | en_US |
dc.format.extent | 966439 bytes | |
dc.format.extent | 3118 bytes | |
dc.format.mimetype | application/pdf | |
dc.format.mimetype | text/plain | |
dc.language.iso | en_US | |
dc.publisher | Elsevier | en_US |
dc.title | Electrochemical reduction of thymine in dimethyl sulfoxide autoprotonation of the radical anion and reduced free radical | en_US |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | en_US |
dc.subject.hlbsecondlevel | Materials Science and Engineering | en_US |
dc.subject.hlbsecondlevel | Chemistry | en_US |
dc.subject.hlbsecondlevel | Chemical Engineering | en_US |
dc.subject.hlbtoplevel | Science | en_US |
dc.subject.hlbtoplevel | Engineering | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | University of Michigan, Ann Arbor, MI 48109 U.S.A. | en_US |
dc.contributor.affiliationother | University of Miami, Coral Gables, FL 33124 U.S.A. | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/23490/1/0000444.pdf | en_US |
dc.identifier.doi | http://dx.doi.org/10.1016/0368-1874(79)87177-4 | en_US |
dc.identifier.source | Journal of Electroanalytical Chemistry | en_US |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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