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Publication Date
2024-5
First Advisor
Alexandra E. Strom
Document Type
Honors Project
Degree Name
Bachelor of Arts
Department
Chemistry
Keywords
linear free energy relationships, mechanistic study, iron catalysis, Hammett plots, competition experiements, α-Amination
Abstract
Linear free energy relationships, such as the Hammett relationship and the Creary relationship, are frequently used as mechanistic probes. One relates the experimentally determined rates of reaction for differently substituted reagents to a predefined set of parameters for the substituents. The parameter set (e.g., Hammett, Hammett+, Hammett–, Creary) that gives the best linearization, and the slope of the linearization, reveal what is happening to the character of the intermediate in the rate determining step and the degree to which substituents affect the rate of reaction. Herein, these relationships are used to explore the rate determining step of the iron catalyzed oxidative α-amination of benzyl ketones with primary and secondary sulfonamides. The determined linearization will suggest whether the reaction proceeds via an α-carbocation, α-radical, and/or other reaction intermediates.
Rights
©2024 Nina Hollin. Access limited to the Smith College community and other researchers while on campus. Smith College community members also may access from off-campus using a Smith College log-in. Other off-campus researchers may request a copy through Interlibrary Loan for personal use.
Language
English
Recommended Citation
Hollin, Nina, "Linear Free Energy Relationships of the Iron- Catalyzed Oxidative α-Amination of Ketones" (2024). Honors Project, Smith College, Northampton, MA.
https://scholarworks.smith.edu/theses/2626
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Comments
71 pages: color illustrations, charts. Includes bibliographical references (pages 51-53).