Open-Resonance-Assisted Hydrogen Bonds and Competing Quasiaromaticity.
Open-Resonance-Assisted Hydrogen Bonds and Competing Quasiaromaticity.
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开放共振辅助氢键和竞争准芳香性。
DOI：
10.1021/acs.joc.8b01331
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发表时间：
2018
期刊：
影响因子：
--
通讯作者：
Brett VanVeller
中科院分区：
文献类型：
--
作者：
Y. Nguyen;Bryan J. Lampkin;A. Venkatesh;A. Ellern;Aaron J. Rossini;Brett VanVeller
质子在共轭桥上互变异构时电子密度的离域可以改变氢键的强度。这种效应被称为共振辅助氢键（RAHB），在互变异构平衡的能量学中起着重要作用。本工作的目的是研究π离域通过参与其他异构化过程在rahb稳定性中的作用。同样，酸碱化学在RAHB的研究中很少受到实验关注，我们解决了酸碱效应在互变异构平衡中的作用。我们发现π离域和邻芳环的断裂是决定RAHB稳定性的主要影响因素。
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.
影响因子：
4.2
作者：
Hu J;Jing H;Lin H
通讯作者：
Lin H