To contribute to the body of knowledge of chemical systems related to molecular machines, the coordination ratios of various boronic acid derivatives and picoline were studied. Several different boroxines and boronates were synthesized using two methods with varying success. The boroxines were synthesized using both a heating mantle method and a microwave assisted method. The boronates were only synthesized using the microwave assisted method. The boroxine synthesis was more complete using the microwave method but there were other issues that caused many of the boroxines to be unsuitable for this study. The boronates were too impure to use as they were, and purification techniques were employed. Silica, paper, and alumina chromatography were all unable to separate the starting materials from the products. Boroxines were chosen as the molecule of choice for this study as the purity could be corrected for more easily. To determine the coordination ratio between any boroxine and picoline, a Job’s plot method was used. Based on the Job’s plot for 4-methoxytriphenylboroxine:Picoline, the coordination ratio for that system is 1:1. All other boroxines were too sensitive to water to be used with this method. Suggestions for future studies with these systems are discussed.