Synthesis and study of some novel and interesting cyclophanes
Thesis (Ph.D.)-- Memorial University of Newfoundland, 2000. Chemistry Includes bibliographical references. The somewhat vague title of this thesis is due to the fact that several fairly loosely-connected projects were investigated, the common thread being the classification of all the targets as &qu...
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ftmemorialunivdc:oai:collections.mun.ca:theses3/150733 2023-05-15T17:23:32+02:00 Synthesis and study of some novel and interesting cyclophanes Houghton, Tom J., 1965- Memorial University of Newfoundland. Dept. of Chemistry 1999. xvii, 240 leaves : ill. Image/jpg; Application/pdf http://collections.mun.ca/cdm/ref/collection/theses3/id/150733 eng eng Electronic Theses and Dissertations (24.07 MB) -- http://collections.mun.ca/PDFs/theses/Houghton_TomJ.pdf a1476690 http://collections.mun.ca/cdm/ref/collection/theses3/id/150733 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 Cyclophanes--Synthesis Text Electronic thesis or dissertation 1999 ftmemorialunivdc 2015-08-06T19:20:21Z Thesis (Ph.D.)-- Memorial University of Newfoundland, 2000. Chemistry Includes bibliographical references. The somewhat vague title of this thesis is due to the fact that several fairly loosely-connected projects were investigated, the common thread being the classification of all the targets as "cyclophanes". [For a definition of this term see Chapter 1.] This approach has naturally had its disadvantages, but it has allowed the author the opportunity to explore some fascinating concepts and methodologies. -- The idea of a tethered-cyclophane-based molecular switch was investigated in Chapter 2. This work led to a new thiacyclophane-forming methodology, and ultimately to the observation of the desired syn-anti equilibrium process sought at the outset. This process was studied by dynamic NMR, and the thermodynamic data for the process, including the transition state, calculated. -- The previous project was expanded to the study of cyclophanes and pyrenophanes bridged by crown ether tethers. Two tethers were used, corresponding to 15-crown-5 and 18-crown-6. The target compounds were successfully synthesised and their conformational properties predicted by computational studies and observed by NMR. -- Two C2-symmetric chiral tetra-functionalised [2.2]paracyclophanes were synthesised, paving the way for the synthesis of some interesting chiral ligands. In the course of this study a much-simplified and very economical apparatus for flash vacuum thermolysis was developed. -- A dithiatetraynophane, a tetraynophane and an enediynophane were synthesised. -- Finally, a new class of "esterophane" was synthesised. The structural features of one example were studied by X-ray crystallography, and a computational analysis performed. 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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ftmemorialunivdc |
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English |
topic |
Cyclophanes--Synthesis |
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Cyclophanes--Synthesis Houghton, Tom J., 1965- Synthesis and study of some novel and interesting cyclophanes |
topic_facet |
Cyclophanes--Synthesis |
description |
Thesis (Ph.D.)-- Memorial University of Newfoundland, 2000. Chemistry Includes bibliographical references. The somewhat vague title of this thesis is due to the fact that several fairly loosely-connected projects were investigated, the common thread being the classification of all the targets as "cyclophanes". [For a definition of this term see Chapter 1.] This approach has naturally had its disadvantages, but it has allowed the author the opportunity to explore some fascinating concepts and methodologies. -- The idea of a tethered-cyclophane-based molecular switch was investigated in Chapter 2. This work led to a new thiacyclophane-forming methodology, and ultimately to the observation of the desired syn-anti equilibrium process sought at the outset. This process was studied by dynamic NMR, and the thermodynamic data for the process, including the transition state, calculated. -- The previous project was expanded to the study of cyclophanes and pyrenophanes bridged by crown ether tethers. Two tethers were used, corresponding to 15-crown-5 and 18-crown-6. The target compounds were successfully synthesised and their conformational properties predicted by computational studies and observed by NMR. -- Two C2-symmetric chiral tetra-functionalised [2.2]paracyclophanes were synthesised, paving the way for the synthesis of some interesting chiral ligands. In the course of this study a much-simplified and very economical apparatus for flash vacuum thermolysis was developed. -- A dithiatetraynophane, a tetraynophane and an enediynophane were synthesised. -- Finally, a new class of "esterophane" was synthesised. The structural features of one example were studied by X-ray crystallography, and a computational analysis performed. |
author2 |
Memorial University of Newfoundland. Dept. of Chemistry |
format |
Thesis |
author |
Houghton, Tom J., 1965- |
author_facet |
Houghton, Tom J., 1965- |
author_sort |
Houghton, Tom J., 1965- |
title |
Synthesis and study of some novel and interesting cyclophanes |
title_short |
Synthesis and study of some novel and interesting cyclophanes |
title_full |
Synthesis and study of some novel and interesting cyclophanes |
title_fullStr |
Synthesis and study of some novel and interesting cyclophanes |
title_full_unstemmed |
Synthesis and study of some novel and interesting cyclophanes |
title_sort |
synthesis and study of some novel and interesting cyclophanes |
publishDate |
1999 |
url |
http://collections.mun.ca/cdm/ref/collection/theses3/id/150733 |
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 (24.07 MB) -- http://collections.mun.ca/PDFs/theses/Houghton_TomJ.pdf a1476690 http://collections.mun.ca/cdm/ref/collection/theses3/id/150733 |
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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1766113152981794816 |