The chemical polymerization of pyrryl Mannich base methiodide salt to porphyrins
Thesis (M.Sc.)--Memorial University of Newfoundland. 1975. Chemistry Bibliography: leaves 52-55. Pyrryl Mannich base methiodides were polymerized in both anhydrous hydroxylic and nonhydroxylic solvents with the hope of clarifying some aspects of the mechanism of porphyrin formation. Although a mixtu...
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ftmemorialunivdc:oai:collections.mun.ca:theses2/242356 2023-05-15T17:23:34+02:00 The chemical polymerization of pyrryl Mannich base methiodide salt to porphyrins Er, Song-Swee Memorial University of Newfoundland. Dept. of Chemistry 1974 55 leaves : ill. Image/jpeg; Application/pdf http://collections.mun.ca/cdm/ref/collection/theses2/id/242356 Eng eng Electronic Theses and Dissertations (19.83 MB) -- http://collections.mun.ca/PDFs/theses/Er_Song-Swee.pdf 76005789 http://collections.mun.ca/cdm/ref/collection/theses2/id/242356 The author retains copyright ownership and moral rights in this thesis. Neither the thesis nor substantial extracts from it may be printed or otherwise reproduced without the author's permission. Paper copy kept in the Centre for Newfoundland Studies, Memorial University Libraries Pyrroles Porphyrins Polymerization Salts Text Electronic thesis or dissertation 1974 ftmemorialunivdc 2015-08-06T19:17:32Z Thesis (M.Sc.)--Memorial University of Newfoundland. 1975. Chemistry Bibliography: leaves 52-55. Pyrryl Mannich base methiodides were polymerized in both anhydrous hydroxylic and nonhydroxylic solvents with the hope of clarifying some aspects of the mechanism of porphyrin formation. Although a mixture of type isomers were obtained, the product composition was found to consist of ~ 95% type (III and IV) and ~ 5% type (I and II) isomers from various solvents. The results suggested that the isomer composition is not dependent on the presence of “active” hydrogen in the solvent, and polymerization is not due to separation of formaldehyde (or equivalent) from the pyrrole and then a “random” polymerization; formation of type III and IV porphyrins is an inherent property of trimethylaminopyrrole salts and rearrangement in some form is a normal part of polymerization. On the basis of these results and published data, an intermediate with ring D porphobilinogen unit in the pyrrolenine form at right angles to the macrocycle formed from the other three pyrrole units and methane bridges is suggested and a scheme for the natural type III porphyrin formation is also proposed. - A new compound diethyl 2,5-dimethyl-3,6-pyrazine-dithiolcarboxylate is reported as a by-product of a pyrryl thiolester synthesis. Thesis Newfoundland studies University of Newfoundland Memorial University of Newfoundland: Digital Archives Initiative (DAI) |
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Memorial University of Newfoundland: Digital Archives Initiative (DAI) |
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English |
topic |
Pyrroles Porphyrins Polymerization Salts |
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Pyrroles Porphyrins Polymerization Salts Er, Song-Swee The chemical polymerization of pyrryl Mannich base methiodide salt to porphyrins |
topic_facet |
Pyrroles Porphyrins Polymerization Salts |
description |
Thesis (M.Sc.)--Memorial University of Newfoundland. 1975. Chemistry Bibliography: leaves 52-55. Pyrryl Mannich base methiodides were polymerized in both anhydrous hydroxylic and nonhydroxylic solvents with the hope of clarifying some aspects of the mechanism of porphyrin formation. Although a mixture of type isomers were obtained, the product composition was found to consist of ~ 95% type (III and IV) and ~ 5% type (I and II) isomers from various solvents. The results suggested that the isomer composition is not dependent on the presence of “active” hydrogen in the solvent, and polymerization is not due to separation of formaldehyde (or equivalent) from the pyrrole and then a “random” polymerization; formation of type III and IV porphyrins is an inherent property of trimethylaminopyrrole salts and rearrangement in some form is a normal part of polymerization. On the basis of these results and published data, an intermediate with ring D porphobilinogen unit in the pyrrolenine form at right angles to the macrocycle formed from the other three pyrrole units and methane bridges is suggested and a scheme for the natural type III porphyrin formation is also proposed. - A new compound diethyl 2,5-dimethyl-3,6-pyrazine-dithiolcarboxylate is reported as a by-product of a pyrryl thiolester synthesis. |
author2 |
Memorial University of Newfoundland. Dept. of Chemistry |
format |
Thesis |
author |
Er, Song-Swee |
author_facet |
Er, Song-Swee |
author_sort |
Er, Song-Swee |
title |
The chemical polymerization of pyrryl Mannich base methiodide salt to porphyrins |
title_short |
The chemical polymerization of pyrryl Mannich base methiodide salt to porphyrins |
title_full |
The chemical polymerization of pyrryl Mannich base methiodide salt to porphyrins |
title_fullStr |
The chemical polymerization of pyrryl Mannich base methiodide salt to porphyrins |
title_full_unstemmed |
The chemical polymerization of pyrryl Mannich base methiodide salt to porphyrins |
title_sort |
chemical polymerization of pyrryl mannich base methiodide salt to porphyrins |
publishDate |
1974 |
url |
http://collections.mun.ca/cdm/ref/collection/theses2/id/242356 |
genre |
Newfoundland studies University of Newfoundland |
genre_facet |
Newfoundland studies University of Newfoundland |
op_source |
Paper copy kept in the Centre for Newfoundland Studies, Memorial University Libraries |
op_relation |
Electronic Theses and Dissertations (19.83 MB) -- http://collections.mun.ca/PDFs/theses/Er_Song-Swee.pdf 76005789 http://collections.mun.ca/cdm/ref/collection/theses2/id/242356 |
op_rights |
The author retains copyright ownership and moral rights in this thesis. Neither the thesis nor substantial extracts from it may be printed or otherwise reproduced without the author's permission. |
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