Thesis
Discovery of Polymorphism in Cocrystals of 5-Fluorouracil and New Solid Phases Involving Halogenated Catechols
University of Iowa
Bachelor of Science (BS), University of Iowa
Spring 2023
Abstract
Crystal engineering allows researchers to predict and modulate the behavior of molecules leading to improvement of physical properties without changing the intrinsic structure of the molecules. Recent methods of synthesis in the solid state use mechanochemistry to promote the self-assembly of cocrystals. Advantages of solid-state synthesis include meeting several of the 12 principles of green chemistry. Most notably, solid-state synthesis reduces derivatives, minimizes waste, and uses minimal solvent.
This thesis work describes two sets of results. The first project involves three cocrystals of the anticancer agent 5-fluorouracil (5-fu): (5-fu)·(3,3’-bpe), (5-fu)·(4,4’-bpe), and a new polymorph of 2(5-fu)·(2,2’-bpe). We explored possible solvent effects on the two forms of 2(5- fu)·(2,2’-bpe) and report that methanol, 1:1 methanol:ethanol, acetonitrile and ethyl acetate yielded the previously reported form I while ethanol, hexane, isopropyl, and chloroform resulted in form II. Water is also reported as a unique solvent as it produced a mixture of both forms.
In the second part of this thesis, we describe the discovery of three novel cocrystals, (3CC)·(2,2’-bpe) and 3(3CC)·2.5(2,2’-bpe) using 3-chlorocatechol (3CC); and 3-bromocatechol (3BC), (3BC)·(2,2’-bpe) as unsymmetrical templates for potential [2+2] photocycloadditions in the solid state. The products were analyzed using powder and single X-ray diffraction (PXRD and SCXRD).
Details
- Title: Subtitle
- Discovery of Polymorphism in Cocrystals of 5-Fluorouracil and New Solid Phases Involving Halogenated Catechols
- Creators
- Clara Stuedemann
- Contributors
- Claudio Margulis (Advisor) - University of Iowa, ChemistryLeonard MacGillivray (Mentor) - University of Iowa, ChemistryCelymar Ortiz-de León (Mentor)
- Resource Type
- Thesis
- Project Type
- Honors Thesis
- Degree Awarded
- Bachelor of Science (BS), University of Iowa
- Degree in
- Chemistry
- Date degree season
- Spring 2023
- Publisher
- University of Iowa
- Number of pages
- 29 pages
- Copyright
- Copyright © 2023 Clara Stuedemann
- Language
- English
- Academic Unit
- CLAS Honors Theses
- Record Identifier
- 9984414552002771
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