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Brian H. Northrop




Dynamic covalent chemistry aids in the synthesis of large, complex organic materials by allowing for the exchange of many individual subunits until the most thermodynamically stable product is formed often in one high yielding step. The boronate ester condensation reaction is just one example of a reversible, thermodynamically driven reaction that has been used in the synthesis of organic materials like covalent organic frameworks and polygons. These materials have many important and diverse applications and their synthesis and optimization is a rich area of research. Small arylboronate esters are considered the building blocks for the much larger frameworks that can be more difficult to work with and study. It was found that substitution in both ortho positions of phenylboronic acid precursors has a large effect on the conformations that these molecules take. In this project several di-ortho substituted arylboronate esters were studied computationally and synthetically in an attempt to explain the varying substituent effects. Steric repulsion can account for many of the conformational preferences of di-ortho substituted arylboronate esters, however computational analysis suggests that electronic effects are also influential in some cases.



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