The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《The tautomerism of N-heteroaromatic hydroxy compounds. I. Infrared spectra》. Authors are Mason, S. F..The article about the compound:Isoquinolin-6-olcas:7651-82-3,SMILESS:OC1=CC2=C(C=NC=C2)C=C1).Recommanded Product: Isoquinolin-6-ol. Through the article, more information about this compound (cas:7651-82-3) is conveyed.
cf. Gibson, et al., C.A. 50, 3899h. The IR spectra of 37 N-heterocyclic hydroxy compounds have been measured in the O-H, N-H, and double-bond stretching-vibration regions by use of a Perkin-Elmer model 12C spectrometer with a LiF or NaCl prism. The compounds were examined at concentrations of 10-2 to 10-3M in cells of 5 cm. (CCl4) or 1 cm. (CHCl3) thickness in the O-H and N-H regions, and 1 mm. in the double-bond region, and as solids included in pressed KBr disks. The compounds with a OH group α or γ to a ring-N atom absorb in the N-H and C:O stretching vibration regions both in the solid state and in CHCl3 solution, and so possess principally amide structures under these conditions. The remaining compounds have mainly enolic structures in solution, showing absorption due to a free or an intramolecularly H-bonded O-H group. The IR evidence for the zwitterionic structure of the latter group of compounds in the solid state is discussed. The compounds which tautomerize to an amide with a quasi ο-quinonoid structure show an N-H stretching vibration absorption in the range 3360-3420 cm.-1, while their quasi p-quinonoid isomers absorb in the range 3415-45 cm.-1, and their analogs with 5-membered rings in the range 3440-85 cm.-1 The position of the C:O band of such compounds depends upon the structural type and the number of N atoms in the ring carrying the potentially tautomeric OH group. For nuclei similarly substituted, the C:O band of the quasiο-quinonoid amides lies at a higher frequency than that of the quasi p-quinonoid isomers. The structures of some dihydroxy and polyaza compounds are elucidated by means of these correlations.
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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method