Crystal engineering: exploiting variation of sulfur oxidation for the control of the solid state structure of organosulfur compounds

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dc.contributor.advisor Lawrence, Simon E. en
dc.contributor.advisor Maguire, Anita R. en Daly, Carla A. en 2013-07-16T14:25:50Z 2013 2013
dc.identifier.citation Daly, C.A. 2013. Crystal engineering: exploiting variation of sulfur oxidation for the control of the solid state structure of organosulfur compounds. PhD Thesis, University College Cork. en
dc.identifier.endpage 275
dc.description.abstract This thesis is focused on the design and synthesis of a diverse range of novel organosulfur compounds (sulfides, sulfoxides and sulfones), with the objective of studying their solid state properties and thereby developing an understanding of how the molecular structure of the compounds impacts upon their solid state crystalline structure. In particular, robust intermolecular interactions which determine the overall structure were investigated. These synthons were then exploited in the development of a molecular switch. Chapter One provides a brief overview of crystal engineering, the key hydrogen bonding interactions utilized in this work and also a general insight into “molecular machines” reported in the literature of relevance to this work. Chapter Two outlines the design and synthetic strategies for the development of two scaffolds suitable for incorporation of terminal alkynes, organosulfur and ether functionalities, in order to investigate the robustness and predictability of the S=O•••H-C≡C- and S=O•••H-C(α) supramolecular synthons. Crystal structures and a detailed analysis of the hydrogen bond interactions observed in these compounds are included in this chapter. Also the biological activities of four novel tertiary amines are discussed. Chapter Three focuses on the design and synthesis of diphenylacetylene compounds bearing amide and sulfur functionalities, and the exploitation of the N-H•••O=S interactions to develop a “molecular switch”. The crystal structures, hydrogen bonding patterns observed, NMR variable temperature studies and computer modelling studies are discussed in detail. Chapter Four provides the overall conclusions from chapter two and chapter three and also gives an indication of how the results of this work may be developed in the future. Chapter Five contains the full experimental details and spectral characterisation of all novel compounds synthesised in this project, while details of the NCI (National Cancer Institute) biological test results are included in the appendix. en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher University College Cork en
dc.rights © 2013, Carla A. Daly. en
dc.rights.uri en
dc.subject Organosulfur en
dc.subject Molecular switch en
dc.subject Diphenylacetylene en
dc.subject.lcsh Hydrogen bonding en
dc.subject.lcsh Sulfur--Oxidation en
dc.title Crystal engineering: exploiting variation of sulfur oxidation for the control of the solid state structure of organosulfur compounds en
dc.type Doctoral thesis en
dc.type.qualificationlevel Doctoral en
dc.type.qualificationname PhD (Science) en
dc.internal.availability Full text available en Restricted to everyone for five years en
dc.description.version Accepted Version
dc.contributor.funder Science Foundation Ireland en
dc.description.status Not peer reviewed en Chemistry en
dc.check.reason This thesis is due for publication or the author is actively seeking to publish this material en
dc.check.opt-out Not applicable en
dc.thesis.opt-out false *
dc.check.entireThesis Entire Thesis Restricted
dc.check.embargoformat Both hard copy thesis and e-thesis en
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© 2013, Carla A. Daly. Except where otherwise noted, this item's license is described as © 2013, Carla A. Daly.
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