期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 17, 页码 9850-9857出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01331
关键词
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资金
- Iowa State University of Science and Technology
- Pfizer Global ASPIRE Award [WI216840]
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 pi-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 pi-delocalization and the disruption of adjacent aromatic rings is the dominant effect in determining the stability of a RAHB.
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