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dc.contributor.advisorMaitland, Derek J.
dc.contributor.advisorBowen, Richard D.
dc.contributor.authorMahmood, Tariq
dc.date.accessioned2013-12-05T13:53:42Z
dc.date.available2013-12-05T13:53:42Z
dc.date.issued2013-12-05
dc.identifier.urihttp://hdl.handle.net/10454/5746
dc.description.abstractNucleophilic substitution reactions of alkylamines, cyclic alkylamines, and hydroxyalkylamines with 5-substituted-1,4-naphthoquinones have been studied. It has been found that the nature of the solvent employed in the reaction influences the position of mono-substitution at either the 2- or 3-position. Although both regioisomers were produced in all the reactions, protic polar solvents favoured the formation of the 3-regioisomer, whereas non-protic solvents favoured the formation of the 2-regioisomer. It has also been found that formation of 2,3-diaminoalkyl derivatives is normally unlikely. A series of hydroxyalkylamino-1,4-naphthoquinones were also synthesised. The collision-induced dissociation mass spectra of protonated hydroxyalkylamino-1,4- naphthoquinones showed fragmentation patterns which were dependent on the nature and length of the side chain and the presence and nature of the adjacent group on the 3-position on the 1,4-naphthoquinone ring. A total of 27 novel compounds were synthesised during the course of this research, the structures of which were confirmed via 1D and 2D NMR spectroscopy, mass spectrometry (ESI), IR spectroscopy and high resolution mass spectrometry (HRESIMS and HREIMS).en_US
dc.language.isoenen_US
dc.rights<a rel="license" href="http://creativecommons.org/licenses/by-nc-nd/3.0/"><img alt="Creative Commons License" style="border-width:0" src="http://i.creativecommons.org/l/by-nc-nd/3.0/88x31.png" /></a><br />The University of Bradford theses are licenced under a <a rel="license" href="http://creativecommons.org/licenses/by-nc-nd/3.0/">Creative Commons Licence</a>.eng
dc.subject5-amino-1,4-naphthoquinoneen_US
dc.subject5-hydroxy-1,4-naphthoquinoneen_US
dc.subject1,4-naphthoquinoneen_US
dc.subjectJugloneen_US
dc.subjectAziridineen_US
dc.subjectEthanolamineen_US
dc.subjectNucleophilic substitutionen_US
dc.subjectSolvent effectsen_US
dc.subjectNMR spectroscopyen_US
dc.subjectMass spectroscopyen_US
dc.titleAspects of the chemistry of 1,4-naphthoquinones. An investigation of nucleophilic substitution reactions of alkylamines and hydroxyalyklamines on 1,4 napthoquinones and the role of solvent on the position of substitution.en_US
dc.type.qualificationleveldoctoralen_US
dc.publisher.institutionUniversity of Bradfordeng
dc.publisher.departmentDivision of Chemical and Forensic Sciencesen_US
dc.typeThesiseng
dc.type.qualificationnamePhDen_US
dc.date.awarded2012
refterms.dateFOA2018-07-19T12:55:22Z


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