When primary amines are reacted with boroxines in solvents such as diethyl ether or THF, a dative bond forms between the lone pair of electrons on the nitrogen atom and a boron atom in a predictable manner. However, when the highly complexing solvent dioxane is used, evidence of a phenyl displacement reaction has been observed. In this work I examined the effects of a variety of electron donating and withdrawing groups on boroxines, specifically whether or not these groups have an effect on the proposed outcome of the hypothesized phenyl displacement reaction. The types of boroxines and amines were varied as well as their relative ratios. The resulting reaction mixtures were evaluated by 1H-NMR, GC-MS and FT-IR. The nitrogen boron dative bond complex formed rather than the desired phenyl replacement product.