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    Aspects 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.

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    Publication date
    2013-12-05
    Author
    Mahmood, Tariq
    Supervisor
    Maitland, Derek J.
    Bowen, Richard D.
    Keyword
    5-amino-1,4-naphthoquinone
    5-hydroxy-1,4-naphthoquinone
    1,4-naphthoquinone
    Juglone
    Aziridine
    Ethanolamine
    Nucleophilic substitution
    Solvent effects
    NMR spectroscopy
    Mass spectroscopy
    Rights
    Creative Commons License
    The University of Bradford theses are licenced under a Creative Commons Licence.
    Institution
    University of Bradford
    Department
    Division of Chemical and Forensic Sciences
    Awarded
    2012
    
    Metadata
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    Abstract
    Nucleophilic 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).
    URI
    http://hdl.handle.net/10454/5746
    Type
    Thesis
    Qualification name
    PhD
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    Theses

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