Date of Award
Summer 2022
Project Type
Thesis
Program or Major
Chemistry
Degree Name
Master of Science
First Advisor
Christine Caputo
Second Advisor
Marc Boudreau
Third Advisor
Glen Miller
Abstract
Herein, a novel intramolecular N-heterocyclic diazaborole FLP complex utilizing boron(III) as the Lewis acid and a pyridyl nitrogen tether as the Lewis base will be presented. It was postulated that the formation of NHBmes can occur after reducing a 1,2-bis(imino)acenaphthenequinone based α-diimine to the dianionic α-diamine by a strong reducing agent like metallic sodium. Efforts to reduce the diimine were successful; however, subsequent attempts to form NHBmes using a 3-coordinate borane were slow and low-yielding. Additional mechanistic elucidation revealed that the first transition state in the formation of NHBmes featured a species that resembled a borinium cation. Consequently, the formation and subsequent addition of a borinium compound to the reduced dianionic diamine yielded more pure NHBmes in more appreciable yields, and its reaction mechanism was elucidated. 1H, 19F, 11B, COSY, DOSY, and HSQC NMR spectroscopy were utilized to characterize the novel NHBmes complex successfully.
Recommended Citation
Moheban, Michael, "The Synthesis and Characterization of Novel N-Heterocyclic Diazaborole Intramolecular Frustrated Lewis Acid/Base Pairs" (2022). Master's Theses and Capstones. 1622.
https://scholars.unh.edu/thesis/1622