Date of Award
2006
Document Type
Thesis
Publication Status
Version of Record
Submission Date
October 2026
Thesis/Dissertation Advisor [Chair]
Lepore, Salvatore D.
Abstract
The synthesis and reactivity of Nucleophile Assisting Leaving Groups was studied in order to assess the rate enhancement of nucleophilic substitution reactions. Various Nucleophile Assisting leaving groups were synthesized, all of them containing a coordinating arm positioned ortho to an electrophilic center on a benzene ring. The various coordinating arms had novel geometries and binding properties. Their reactivity was studied with a variety of metal salts and the kinetics of the reactions was studied with 1H-NMR spectroscopy. This method provided a quantitative measurement of the rate enhancement observed in the substitution reactions from the rate constants obtained. In the case of certain crown ether-containing substrates, NMR experiments suggest that the mechanism of substitution proceeds in two steps, the first being a pre-coordination of the metal salt with the coordinating arm, followed by a conversion of the complex to products.
Extent
110 p.
Recommended Citation
Cohn, Pamela., "synthesis and reactivity of nucleophile assisting leaving groups" (2006). Electronic Theses and Dissertations 2000 - 2009. 1166.
https://digitalcommons.fau.edu/etd_general_5/1166
Identifier
FADT13375
Comments
Thesis (M.S.)--Florida Atlantic University, 2006.|Charles E. Schmidt College of Science|FAU Electronic Theses and Dissertations Collection|Thesis (M.S.)--Florida Atlantic University, 2006.