Date of Award

Summer 2022

Project Type


Program or Major


Degree Name

Master of Science

First Advisor

Christine Caputo

Second Advisor

Marc Boudreau

Third Advisor

Glen Miller


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.