A study of Macrocycle Structure and Reactivity: A curious Reactivity Pattern and Investigation of N,N'-dimethyltribenzo-1,4,7-triazacyclononatriene
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This project’s ultimate goal was to attempt to complex , N,N′-dimethyltribenzo-1,4,7-triazacyclononane, Me2N3-CTV, and N,N’,N”-trimethyltribenzo-1,4,7-triazacyclononane, Me3N3-CTV with CuBr2. This was based on the notion that many other macrocycles bind with transition metal cations. These goals were never accomplished although parallel results to those of previous researched were generated. The products generated from synthesis reactions, to reproduce Beattie’s product, were analyzed to conclude that Beattie’s product was in fact the same as the one generated in this study. This conclusion was made by characterization of various spectra obtained from the isolated product. The reaction of Me2N3-CTV and CuBr2 resulted in a brown crystalline product that was isolated for characterization via the following techniques: UV/Vis, IR, and EPR spectroscopy, but no structure was obtained from X–ray crystallography. X–ray crystallography is crucial for the identification of this product; however, based on previous structure generated by Beattie and spectra collected by both Beattie and Nutile, there is enough evidence to draw upon. It is ultimately the conclusion that there is a suspected rearrangement of the organic macrocycle, Me2N3-CTV, to a radical cation product occurring when reaction occurs with CuBr2.
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