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).
| Identifer | oai:union.ndltd.org:BRADFORD/oai:bradscholars.brad.ac.uk:10454/5746 |
| Date | January 2012 |
| Creators | Mahmood, Tariq |
| Contributors | Maitland, Derek J., Bowen, Richard D. |
| Publisher | University of Bradford, Division of Chemical and Forensic Sciences |
| Source Sets | Bradford Scholars |
| Language | English |
| Detected Language | English |
| Type | Thesis, doctoral, PhD |
| 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>. |
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