Open-Resonance-Assisted Hydrogen Bonds and Competing Quasiaromaticity.
J Org Chem
; 83(17): 9850-9857, 2018 09 07.
Article
en En
| MEDLINE
| ID: mdl-30024169
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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Colección:
01-internacional
Banco de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2018
Tipo del documento:
Article
País de afiliación:
Estados Unidos