The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Activated nucleophilic substitution in aromatic compounds. V. Reactivity of 2-, 3-, and 4-chloropyridine N-oxides with piper[dine in methanol》. Authors are Coppens, G.; Declerck, F.; Gillet, C.; Nasielski, J..The article about the compound:2-Chloropyridine 1-oxidecas:2402-95-1,SMILESS:ClC1=CC=CC=[N+]1[O-]).Synthetic Route of C5H4ClNO. Through the article, more information about this compound (cas:2402-95-1) is conveyed.
cf. CA 50, 11260f. The conductimetrically-measured rates of reaction of 2-, 3-, and 4-chloropyridine N-oxides with piperidine in MeOH solution gave, at 80°, the apparent unimol. rate constants 3.70 ×10-4, 1.04 × 10-7, and 1.02 × 10-4 sec.-1, resp. The reactivity sequence 2 > 4 ≫ 3 was discussed in terms of competing inductive and internal solvation effects.
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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem