{"id":{"repo_id":"london-metro","oai_identifier":"oai:repository.londonmet.ac.uk:2977"},"canonical_url":"https://search.dev.ndltd.org/etd/london-metro/oai:repository.londonmet.ac.uk:2977","repository":{"repo_id":"london-metro","name":"London Metropolitan University","base_url":"https://repository.londonmet.ac.uk/cgi/oai2"},"display":{"title":"Chemistry and biological activity of iron quinoneoximic complexes","abstract":"The synthesis and structure of 1,2-quinone mono-oximes have been reviewed. The reaction of 3-hydroxyphenol, 3-hydroxy-2-aethylphenol, 3-hydroxy-5-methylphenol and N-acetyl-3-aminophenol with amyl nitrite/M(OEt) (M - Na or K) has been systematically examined. It has been found that the complex formed depends on the reaction temperature and phenol/M(OEt) ratio. Infra-red spectroscopic studies have shown that in the solid state 5-hydroxy-l,2-benzoquinone 2-oxime (hqoH,), 5-hydroxy-3-methyl-l,2-benzoquinone 2-oxime (3-MehqoH2), 5-hydroxy-6-methyl-l,2-benzoquinone 2-oxime (e-MehqoH,) and H-acetyl-5-amino- 1,2-benzoquinone 2-oxime (N-AcqoH) and their sodium and potassium complexes exist in the oximic form rather than the nitroso form. Nuclear magnetic resonance studies have also shown that in d,-DHSO solution hqoH,, 3-MehqoH, and 6-MehqoH} and their sodium complexes exist in one form only which is oximic in character. However, in DjO the results for the sodium complexes of hqoH, and e-MeqoH, indicate the presence of at least two species. In the case of the sodium 5-hydroxy-6-methyl-l,2-benzoquinone 2-oximate these species are oximic in character. An X-ray crystallographic study of e-HehqoH, has shown that in the solid state this compound exists in the 1,4- rather than the 1,2-quinone 2-oxlmic form. The synthesis of iron(II) complexes of hqoH,, 3-MehqoH] and 6-HehqoH] using the direct and the nitrosation methods was examined. The direct method gave rise to the complexes Fe(hqoH), OHjO, Fe(3-HehqoH), and Fe(6-MehqoH)2 '2H20 whereas the nitrosation method gave rise to ill-defined solids. Na[Fe(N-Acqo), ]-4H20 was obtained by nitrosation of N-acetyl-3-aminopnenol in the presence of Iron(II) ammonium sulphate. Hossbauer and magnetic studies indicate that Na[Fe(N-Acqo)j]-4H20 is a low spin iron(II) complex whereas the bischelates have properties indicative of the S - 1 spin state. In-vlvo assesment of the iron chelating ability of hqoHj, 3-MehqoH2, 6-MehqoH2, N-AcqoH , N,N-dimethyl-5- amino-1,2-benzoquinone 2-oxime and violuric acid was carried out using a normal rat model. The chelators hqoH, and 6-HehqoH2were found to be effective in removing iron when administered intra-muscularly but they also caused the excretion of magnesium. Their activity was lower than that of desferrioxamine and neither was effective when administered orally.","abstract_html":"The synthesis and structure of 1,2-quinone mono-oximes have been reviewed. The reaction of 3-hydroxyphenol, 3-hydroxy-2-aethylphenol, 3-hydroxy-5-methylphenol and N-acetyl-3-aminophenol with amyl nitrite/M(OEt) (M - Na or K) has been systematically examined. It has been found that the complex formed depends on the reaction temperature and phenol/M(OEt) ratio. Infra-red spectroscopic studies have shown that in the solid state 5-hydroxy-l,2-benzoquinone 2-oxime (hqoH,), 5-hydroxy-3-methyl-l,2-benzoquinone 2-oxime (3-MehqoH2), 5-hydroxy-6-methyl-l,2-benzoquinone 2-oxime (e-MehqoH,) and H-acetyl-5-amino- 1,2-benzoquinone 2-oxime (N-AcqoH) and their sodium and potassium complexes exist in the oximic form rather than the nitroso form. Nuclear magnetic resonance studies have also shown that in d,-DHSO solution hqoH,, 3-MehqoH, and 6-MehqoH} and their sodium complexes exist in one form only which is oximic in character. However, in DjO the results for the sodium complexes of hqoH, and e-MeqoH, indicate the presence of at least two species. In the case of the sodium 5-hydroxy-6-methyl-l,2-benzoquinone 2-oximate these species are oximic in character. An X-ray crystallographic study of e-HehqoH, has shown that in the solid state this compound exists in the 1,4- rather than the 1,2-quinone 2-oxlmic form. The synthesis of iron(II) complexes of hqoH,, 3-MehqoH] and 6-HehqoH] using the direct and the nitrosation methods was examined. The direct method gave rise to the complexes Fe(hqoH), OHjO, Fe(3-HehqoH), and Fe(6-MehqoH)2 '2H20 whereas the nitrosation method gave rise to ill-defined solids. Na[Fe(N-Acqo), ]-4H20 was obtained by nitrosation of N-acetyl-3-aminopnenol in the presence of Iron(II) ammonium sulphate. Hossbauer and magnetic studies indicate that Na[Fe(N-Acqo)j]-4H20 is a low spin iron(II) complex whereas the bischelates have properties indicative of the S - 1 spin state. In-vlvo assesment of the iron chelating ability of hqoHj, 3-MehqoH2, 6-MehqoH2, N-AcqoH , N,N-dimethyl-5- amino-1,2-benzoquinone 2-oxime and violuric acid was carried out using a normal rat model. The chelators hqoH, and 6-HehqoH2were found to be effective in removing iron when administered intra-muscularly but they also caused the excretion of magnesium. Their activity was lower than that of desferrioxamine and neither was effective when administered orally.","abstract_has_math":false,"creators":["Pathirana, Navin Deepal."],"institution":"Polytechnic of North London","degree_name":"phd","degree_level":"doctoral","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":1990,"date_issued":"1990-03","date_published":"1990-03","updated_at":"2026-07-24T02:54:27Z","subjects":["540 Chemistry & allied sciences"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier.grantnumber","label":"Dc Identifier Grantnumber","values":["N/A"],"render_values":[{"text":"N/A","href":null,"code":true}]}]},"links":{"outbound_url":null,"outbound_label":null,"outbound_source":null},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.sponsor","label":"Sponsor","values":["London Metropolitan University"]},{"key":"dc:creator","label":"Author","values":["Pathirana, Navin Deepal."]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["1990-03"]},{"key":"dc:date.issued","label":"Date","values":["1990-03"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["School of Human Sciences (SHSC)","Department of Applied Chemistry and Life Sciences"]},{"key":"dc:publisher.institution","label":"Dc Publisher Institution","values":["Polytechnic of North London"]},{"key":"dc:relation.isreferencedby","label":"Dc Relation Isreferencedby","values":["https://repository.londonmet.ac.uk/2977/"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"dc:type.qualificationlevel","label":"Dc Type Qualificationlevel","values":["doctoral"]},{"key":"dc:type.qualificationname","label":"Dc Type Qualificationname","values":["phd"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["540 Chemistry & allied sciences"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.grantnumber","label":"Dc Identifier Grantnumber","values":["N/A"]},{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://repository.londonmet.ac.uk/2977/1/252939.pdf"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The synthesis and structure of 1,2-quinone mono-oximes have been reviewed. The reaction of 3-hydroxyphenol, 3-hydroxy-2-aethylphenol, 3-hydroxy-5-methylphenol and N-acetyl-3-aminophenol with amyl nitrite/M(OEt) (M - Na or K) has been systematically examined. It has been found that the complex formed depends on the reaction temperature and phenol/M(OEt) ratio. Infra-red spectroscopic studies have shown that in the solid state 5-hydroxy-l,2-benzoquinone 2-oxime (hqoH,), 5-hydroxy-3-methyl-l,2-benzoquinone 2-oxime (3-MehqoH2), 5-hydroxy-6-methyl-l,2-benzoquinone 2-oxime (e-MehqoH,) and H-acetyl-5-amino- 1,2-benzoquinone 2-oxime (N-AcqoH) and their sodium and potassium complexes exist in the oximic form rather than the nitroso form. Nuclear magnetic resonance studies have also shown that in d,-DHSO solution hqoH,, 3-MehqoH, and 6-MehqoH} and their sodium complexes exist in one form only which is oximic in character. However, in DjO the results for the sodium complexes of hqoH, and e-MeqoH, indicate the presence of at least two species. In the case of the sodium 5-hydroxy-6-methyl-l,2-benzoquinone 2-oximate these species are oximic in character. An X-ray crystallographic study of e-HehqoH, has shown that in the solid state this compound exists in the 1,4- rather than the 1,2-quinone 2-oxlmic form. The synthesis of iron(II) complexes of hqoH,, 3-MehqoH] and 6-HehqoH] using the direct and the nitrosation methods was examined. The direct method gave rise to the complexes Fe(hqoH), OHjO, Fe(3-HehqoH), and Fe(6-MehqoH)2 '2H20 whereas the nitrosation method gave rise to ill-defined solids. Na[Fe(N-Acqo), ]-4H20 was obtained by nitrosation of N-acetyl-3-aminopnenol in the presence of Iron(II) ammonium sulphate. Hossbauer and magnetic studies indicate that Na[Fe(N-Acqo)j]-4H20 is a low spin iron(II) complex whereas the bischelates have properties indicative of the S - 1 spin state. In-vlvo assesment of the iron chelating ability of hqoHj, 3-MehqoH2, 6-MehqoH2, N-AcqoH , N,N-dimethyl-5- amino-1,2-benzoquinone 2-oxime and violuric acid was carried out using a normal rat model. The chelators hqoH, and 6-HehqoH2were found to be effective in removing iron when administered intra-muscularly but they also caused the excretion of magnesium. Their activity was lower than that of desferrioxamine and neither was effective when administered orally."]},{"key":"dc:format","label":"Dc Format","values":["text"]},{"key":"dc:title","label":"Title","values":["Chemistry and biological activity of iron quinoneoximic complexes"]}]}],"canonical_facts":{"dc:contributor.sponsor":["London Metropolitan University"],"dc:creator":["Pathirana, Navin Deepal."],"dc:date":["1990-03"],"dc:date.issued":["1990-03"],"dc:description.abstract":["The synthesis and structure of 1,2-quinone mono-oximes have been reviewed. The reaction of 3-hydroxyphenol, 3-hydroxy-2-aethylphenol, 3-hydroxy-5-methylphenol and N-acetyl-3-aminophenol with amyl nitrite/M(OEt) (M - Na or K) has been systematically examined. It has been found that the complex formed depends on the reaction temperature and phenol/M(OEt) ratio. Infra-red spectroscopic studies have shown that in the solid state 5-hydroxy-l,2-benzoquinone 2-oxime (hqoH,), 5-hydroxy-3-methyl-l,2-benzoquinone 2-oxime (3-MehqoH2), 5-hydroxy-6-methyl-l,2-benzoquinone 2-oxime (e-MehqoH,) and H-acetyl-5-amino- 1,2-benzoquinone 2-oxime (N-AcqoH) and their sodium and potassium complexes exist in the oximic form rather than the nitroso form. Nuclear magnetic resonance studies have also shown that in d,-DHSO solution hqoH,, 3-MehqoH, and 6-MehqoH} and their sodium complexes exist in one form only which is oximic in character. However, in DjO the results for the sodium complexes of hqoH, and e-MeqoH, indicate the presence of at least two species. In the case of the sodium 5-hydroxy-6-methyl-l,2-benzoquinone 2-oximate these species are oximic in character. An X-ray crystallographic study of e-HehqoH, has shown that in the solid state this compound exists in the 1,4- rather than the 1,2-quinone 2-oxlmic form. The synthesis of iron(II) complexes of hqoH,, 3-MehqoH] and 6-HehqoH] using the direct and the nitrosation methods was examined. The direct method gave rise to the complexes Fe(hqoH), OHjO, Fe(3-HehqoH), and Fe(6-MehqoH)2 '2H20 whereas the nitrosation method gave rise to ill-defined solids. Na[Fe(N-Acqo), ]-4H20 was obtained by nitrosation of N-acetyl-3-aminopnenol in the presence of Iron(II) ammonium sulphate. Hossbauer and magnetic studies indicate that Na[Fe(N-Acqo)j]-4H20 is a low spin iron(II) complex whereas the bischelates have properties indicative of the S - 1 spin state. In-vlvo assesment of the iron chelating ability of hqoHj, 3-MehqoH2, 6-MehqoH2, N-AcqoH , N,N-dimethyl-5- amino-1,2-benzoquinone 2-oxime and violuric acid was carried out using a normal rat model. The chelators hqoH, and 6-HehqoH2were found to be effective in removing iron when administered intra-muscularly but they also caused the excretion of magnesium. Their activity was lower than that of desferrioxamine and neither was effective when administered orally."],"dc:format":["text"],"dc:identifier.grantnumber":["N/A"],"dc:identifier.uri":["https://repository.londonmet.ac.uk/2977/1/252939.pdf"],"dc:publisher.department":["School of Human Sciences (SHSC)","Department of Applied Chemistry and Life Sciences"],"dc:publisher.institution":["Polytechnic of North London"],"dc:relation.isreferencedby":["https://repository.londonmet.ac.uk/2977/"],"dc:subject":["540 Chemistry & allied sciences"],"dc:title":["Chemistry and biological activity of iron quinoneoximic complexes"],"dc:type":["Thesis"],"dc:type.qualificationlevel":["doctoral"],"dc:type.qualificationname":["phd"]},"updated_at":"2026-07-24T02:54:27Z"}