The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Novel spiroborates and a dipole moment study of 1,3,2 dioxaboraazulene-2-spiro-2′-(1′,3′,2′-benzodioxaborole)》. Authors are Balaban, A. T.; Bally, Ioana; Bishop, R. J.; Rentea, C. N.; Sutton, L. E..The article about the compound:8-Hydroxyquinoline 1-oxidecas:1127-45-3,SMILESS:OC1=CC=CC2=CC=C[N+]([O-])=C12).Application of 1127-45-3. Through the article, more information about this compound (cas:1127-45-3) is conveyed.
The large dipole moment (8.24 D.) of 5(7)-methyl-1,3,2-dioxaboraazulene-2-spiro-2′-(1′,3′,2′-benzodioxaborole) (I) confirms the spiran co-ordinated structure previously suggested. Stable spiroborates are formed from butoxy-benzodioxaborole with 8-hydroxyquinoline or its N-oxide, but not with 3-hydroxy-γ-pyrone.
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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider