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dc.contributor.authorHayat, Nadia
dc.contributor.authorFenwick, Nathan W.
dc.contributor.authorSaidykhan, Amie
dc.contributor.authorTelford, Richard
dc.contributor.authorMartin, William H.C.
dc.contributor.authorGallagher, R.T.
dc.contributor.authorBowen, Richard D.
dc.date.accessioned2019-10-15T13:50:37Z
dc.date.accessioned2019-11-05T09:07:29Z
dc.date.available2019-10-15T13:50:37Z
dc.date.available2019-11-05T09:07:29Z
dc.date.issued2019-12-01
dc.identifier.citationHayat N, Fenwick NW, Saidykhan A, Telford R et al (2019) Structure reactivity relationship in the accelerated formation of 2,3-diarylquinoxalines in the microdroplets of a nebuliser. European Journal of Mass Spectrometry. 25(6): 457-462.en_US
dc.identifier.urihttp://hdl.handle.net/10454/17409
dc.descriptionNoen_US
dc.description.abstractCompetition experiments in which 1,2-phenylenediamine, C6H4(NH2)2, condenses with equimolar quantities of benzil, (C6H5CO)2, and a 3,3'- or 4,4'-disubstituted benzil (XC6H4CO)2 (X = F, Cl, Br, CH3 or CH3O) to form a mixture of 2,3-diphenylquinoxaline and the corresponding 2,3-diarylquinoxaline (Ar = XC6H4) in the microdroplets produced in a nebuliser allow a Hammett relationship with a ρ value of 1.85 to be developed for this accelerated condensation in the nebuliser. This structure reactivity relationship reveals that an appreciable amount of negative charge builds up on the carbon of the carbonyl group of the benzil during the rate-limiting step of the reaction, thus confirming that this process involves nucleophilic addition of the 1,2-phenylenediamine to the benzil. In general, the presence of an electron donating substituent, particularly in the 4 and 4' positions, in the benzil retards the reaction, whereas an electron attracting substituent, especially in the 3 and 3' position, accelerates it.en_US
dc.description.sponsorship2019 British Mass Spectrometry Summer Studentship for NWF.en_US
dc.language.isoenen_US
dc.relation.isreferencedbyhttps://doi.org/10.1177/1469066719877346en_US
dc.subjectDiarylquinoxalinesen_US
dc.subjectHammett relationshipen_US
dc.subjectCondensationen_US
dc.subjectElectrosprayen_US
dc.subjectNebuliseren_US
dc.titleStructure reactivity relationship in the accelerated formation of 2,3-diarylquinoxalines in the microdroplets of a nebuliseren_US
dc.status.refereedYesen_US
dc.date.Accepted2019-08-29
dc.date.application2019-09-23
dc.typeLetteren_US
dc.type.versionNo full-text in the repositoryen_US
dc.date.updated2019-10-15T12:50:39Z
refterms.dateFOA2019-11-05T09:11:19Z


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