The discipline of physical organic chemistry (POC) has historically had an emphasis on deciphering organic reaction mechanisms, characterizing reactive intermediates, and working out reaction coordinates. The experimental tools of the trade have been used in many other areas: biochemistry, organometallic chemistry, and materials chemistry. Yet, knowledge of organic reaction mechanisms and use of techniques such as kinetics and spectroscopy can have an impact on the analytical sciences. In this regard, we recently studied a paradigmatic boronic-acid sensor for carbohydrates, and revealed that the photophysics principle which leads to emission turn-on is an unanticipated “loose-bolt” effect. Our group has also applied POC strategies to understand the optical response from rapid detection methods for enantiomeric excess (ee), and more recently diastereomeric ratio (dr). In the most recent example, machine learning techniques have been applied to extract the ee and dr during reaction screening. In addition, using knowledge of organic reaction mechanisms we have devised a series of self-inductive cascades that led to the classification of V- and G-nerve agents. Further, by analyzing reactivity trends we were able to control Tunable Orthogonal Reversible Covalent (TORC) bonds for the generation of polymeric structures whose properties can be triggered to morph and ultimately degrade entirely in response to analytes. Each of these individual projects will be discussed to demonstrate the power of a union of POC with analytical chemistry.

Award Address (James Flack Norris Award in Physical Organic Chemistry sponsored by the ACS Northeastern Section). Physical organic chemistry in the analytical sciences

2019 Spring National Meeting

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