Graduate Program
Chemistry
Degree Name
Master of Science (MS)
Semester of Degree Completion
2011
Thesis Director
Kraig Wheeler
Thesis Committee Member
Steven Daniels
Thesis Committee Member
Unknown
Abstract
Controlling chemical processes and directing product formation has been a long sought-after goal of synthetic chemists. Most synthesis techniques focus on reactions performed in solution. Such traditional approaches have several disadvantages including unwanted side products, disrupting chemical processes and low reaction yields. A proposed approach to circumvent these drawbacks focuses on performing reactions in the solid state. This method promises better control and higher reaction yields due to the controlled environment of the reaction components. Because molecules in the solid state are effectively fixed, reactions can be performed with a high degree of selectivity, reducing side products and eliminating unwanted chemical processes.
One such method utilizes adjacent C=C, bonds which when properly aligned, can be induced into reacting with one another to form cyclobutane rings. Such techniques have demonstrated that heteromeric molecular pairs can be designed for solid-state reaction to form macromolecules with specifically tailored composition. By using racemic and quasiracemic mixtures the effectiveness and application of such methods can be investigated. In particular, quasiracemates allow exploration of new ways of synthesizing molecules with intriguing stereochemical properties. Controlling the stereochemical nature of reactions is inherently a very difficult task and this investigation hopes to shed more light on research in this area.
We have investigated the effectiveness of UV induced cycloaddition reactions using racemates and quasiracemates. Results from this study have shown that given the proper alignment in the solid state, adjacent C=C groups can be reacted to form cyclobutane groups. This is primarily achieved by use of heteromeric pairs organized in molecular crystals. The resulting individual molecules as well as the extended molecular framework have shed light on new possibilities in material and synthetic science.
Recommended Citation
Zinovchik, Sergey, "Structural And Photochemical Behavior Of Phenyl And Dihydrophenyl Sulfonamidecinnamic Acids" (2011). Masters Theses. 80.
https://thekeep.eiu.edu/theses/80
