Campus Units

Chemistry

Document Type

Article

Publication Version

Submitted Manuscript

Publication Date

7-19-2018

Journal or Book Title

The Journal of Organic Chemistry

DOI

10.1021/acs.joc.8b01331

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.

Comments

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.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

Published Version

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