Journal or Book Title
The Journal of Organic Chemistry
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.
American Chemical Society
Nguyen, Yen H.; Lampkin, Bryan J.; Venkatesh, Amrit; Ellern, Arkady; Rossini, Aaron J.; and VanVeller, Brett, "Open Resonance Assisted Hydrogen Bonds and Competing Quasiaromaticity" (2018). Chemistry Publications. 1036.