The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《On prediction of OH stretching frequencies in intramolecularly hydrogen bonded systems》. Authors are Hansen, Poul Erik; Spanget-Larsen, Jens.The article about the compound:8-Hydroxyquinoline 1-oxidecas:1127-45-3,SMILESS:OC1=CC=CC2=CC=C[N+]([O-])=C12).Category: quinoxaline. Through the article, more information about this compound (cas:1127-45-3) is conveyed.
OH stretching frequencies are investigated for a series of non-tautomerizing systems with intramol. hydrogen bonds. Effective OH stretching wavenumbers are predicted by the application of empirical correlation procedures based on the results of B3LYP/6-31G(d) theor. calculations in the harmonic and PT2 anharmonic approximations, as well as on exptl. NMR parameters, i.e., proton chem. shifts (δ H) and two-bond deuterium isotope effects on 13C chem. shifts (2ΔCOD). The procedures are applied in a discussion of the spectra of 2,6-dihydroxy-4-methylbenzaldehyde and 8-hydroxyquinoline N-oxide. The spectrum of the former displays a broad, composite band between 3500 and 2500 cm-1 which can be assigned to overlapping monomer and dimer contributions. In the latter case, the results support a reassignment of the OH stretching band of 8-hydroxyquinoline N-oxide; the reassignment is supported by correlation with the IR spectra of a series of substituted derivatives
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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider