Open-Resonance-Assisted Hydrogen Bonds and Competing Quasiaromaticity
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The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).
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The Department of Chemistry was founded in 1880.
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1880-present
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- College of Liberal Arts and Sciences (parent college)
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Abstract
The delocalization of electron density upon tautomerization of a proton across a conjugated bridge can alter the strength of hydrogen bonds. This effect has been dubbed resonance-assisted hydrogen bonding (RAHB) and plays a major role in the energetics of the tautomeric equilibrium. The goal of this work was to investigate the role that π-delocalization plays in the stability of RAHBs by engaging other isomerization processes. Similarly, acid-base chemistry has received little experimental attention in studies of RAHB and we address the role that acid-base effects play in the tautomeric equilibrium. We find that π-delocalization and the disruption of adjacent aromatic rings is the dominant effect in determining the stability of a RAHB.
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This is a manuscript of an article published as Nguyen, Yen H., Bryan J. Lampkin, Amrit Venkatesh, Arkady Ellern, Aaron J. Rossini, and Brett VanVeller. "Open-Resonance-Assisted Hydrogen Bonds and Competing Quasiaromaticity." The Journal of Organic Chemistry (2018). Posted with permission.