Open-Resonance-Assisted Hydrogen Bonds and Competing Quasiaromaticity was written by Nguyen, Yen H.;Lampkin, Bryan J.;Venkatesh, Amrit;Ellern, Arkady;Rossini, Aaron J.;VanVeller, Brett. And the article was included in Journal of Organic Chemistry in 2018.Formula: C8H5ClN2 This article mentions the following:
The delocalization of electron d. 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 chem. has received little exptl. 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. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Formula: C8H5ClN2).
6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxalines are important class of heterocyclic compounds, associated with wider pharmacological applications. Quinoxaline and its analogues may also be formed by reduction of amino acids substituted 1,5-difluoro-2,4-dinitrobenzene (DFDNB),One study used 2-iodoxybenzoic acid (IBX) as a catalyst in the reaction of benzil with 1,2-diaminobenzene.Formula: C8H5ClN2
Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider