COMPUTATIONAL STUDIES OF DISUBSTITUTED BICYCLO[m.m.m]ALKANE AND DISUBSTITUTED BICYCLO[8.8.n]ALKANES, SYNTHESIS OF 1,10-DIMETHYLBICYCLO[8.8.8]HEXACOSANE AND 1,10-DIHYDROXYBICYCLO[8.8.8]HEXACOSANE, AND PROGRESS TOWARDS THE SYNTHESIS OF A DISUBSTITUTED 1,10-
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Author
Jones, Ian W.Issue Date
2008Keywords
Bicyclo[8.8.8]hexacosaneBicyclo[8.8.n]alkane
Bicyclo[m.m.m]alkane
Conformational Analysis
Elastomer
Novel Polymer
Committee Chair
Mash Jr., Eugene A.
Metadata
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The University of Arizona.Rights
Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.Abstract
Polymers possess bulk elastic properties due to entanglement of the polymer chains, not due to an inherit elasticity found within the monomers. An appropriately disubstituted bicyclo[8.8.8]hexacosane monomer should impart inherit elasticity when utilized in a polymer. A stochastic search of disubstituted bicyclo[m.m.m]alkanes demonstrated that these systems will adopt an out,out configuration and bicycles with medium and large values of m possess variable bridgehead-bridgehead distances. A stochastic search of disubstituted bicyclo[8.8.n]alkanes demonstrated an even-odd effect within the bite-angle of the bicycle. Two model compounds with methyl and hydroxyl groups at the bridgehead carbons were synthesized that demonstrated solid-state structures that correlated extremely well with the computational search. The solid-state structures were observed with both an out,out configuration and variable bridgehead-bridgehead distances. To investigate this hypothesis, polyurethanes will be made from the following diol monomers: 1,10-decanediol, a monocyclic diol, and a bicyclo[8.8.8]hexacosane diol.Type
textElectronic Dissertation
Degree Name
Ph.D.Degree Level
doctoralDegree Program
ChemistryGraduate College
Degree Grantor
University of ArizonaCollections
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