One-electron oxidation of chloroquine, cymanquine, and related aminoquinolines in nonaqueous media

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dc.contributor.authorLam, Kevin
dc.contributor.authorVan Wyck, Stephen J.
dc.contributor.authorGeiger, William E.
dc.creatorKevin, Lam
dc.date.accessioned2017-12-20T03:28:57Z
dc.date.available2017-12-20T03:28:57Z
dc.date.issued2017-08-15
dc.description.abstractAbstract The anodic oxidation of a series of secondary-amine-substituted chloroquinoline derivatives, 1–5, has been studied in dichloromethane/0.05M [NBu4][B(C6F5)4]. Compounds 4 and 5 contain organometallic moieties of the cymantrene family as part of the amine group. All five compounds undergo an electrochemically irreversible one-electron oxidation. For compounds 2–4, this occurs at the secondary amine group (0.86 to 0.98V vs ferrocene). The oxidations of others occur at tertiary amines located either in the side chain of the quinoline secondary amine (1, 0.68V) or in the cyclopentadienyl ring of the cymantrene moiety (5, 0.82V). The anodic reaction products have been isolated and shown to be ring-nitrogen protonated aminochloroquinolinium ions. Abstraction of a hydrogen atom from the solvent by the putative aminochloroquinoline radical cation is thought to be responsible for formation of the protonated oxidation product. Cathodic reduction of the latter regenerates the neutral starting material in an overall chemically reversible process that mimics a simple acid/base reaction at the quinoline ring nitrogen.en_US
dc.identifierDOI:10.1016/j.jelechem.2017.06.041
dc.identifier.citationKevin Lam, Stephen J. Van Wyck, William E. Geiger, One-electron oxidation of chloroquine, cymanquine, and related aminoquinolines in nonaqueous media, In Journal of Electroanalytical Chemistry, Volume 799, 2017, Pages 531-537en_US
dc.identifier.issn15726657
dc.identifier.urihttps://www.sciencedirect.com/science/article/pii/S1572665717304708
dc.identifier.urihttp://nur.nu.edu.kz/handle/123456789/2955
dc.language.isoenen_US
dc.publisherJournal of Electroanalytical Chemistryen_US
dc.relation.ispartofJournal of Electroanalytical Chemistry
dc.rights.license© 2017 Elsevier B.V. All rights reserved.
dc.subjectQuinoline oxidationen_US
dc.subjectRadical cationen_US
dc.subjectH-atom captureen_US
dc.subjectAliphatic amine oxidationen_US
dc.subjectCymantreneen_US
dc.subjectQuinoline-cymantrene conjugateen_US
dc.titleOne-electron oxidation of chloroquine, cymanquine, and related aminoquinolines in nonaqueous mediaen_US
dc.typeArticleen_US
elsevier.aggregationtypeJournal
elsevier.coverdate2017-08-15
elsevier.coverdisplaydate15 August 2017
elsevier.endingpage537
elsevier.identifier.doi10.1016/j.jelechem.2017.06.041
elsevier.identifier.eid1-s2.0-S1572665717304708
elsevier.identifier.piiS1572-6657(17)30470-8
elsevier.identifier.scopusid85022218514
elsevier.openaccess0
elsevier.openaccessarticlefalse
elsevier.openarchivearticlefalse
elsevier.startingpage531
elsevier.teaserThe anodic oxidation of a series of secondary-amine-substituted chloroquinoline derivatives, 1–5, has been studied in dichloromethane/0.05M [NBu4][B(C6F5)4]. Compounds 4 and 5 contain organometallic...
elsevier.volume799
workflow.import.sourcescience

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