The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Nucleophilic heteroaromatic substitution. XXVII. Piperidino dechlorination and methoxy dechlorination of 6- and 8-alkyl-4-chloroquinolines. Steric hindrance to specific solvation》. Authors are Calligaris, Mario; Illuminati, Gabriello; Marino, Gianlorenzo.The article about the compound:4-Chloro-8-methylquinolinecas:18436-73-2,SMILESS:CC1=C2N=CC=C(Cl)C2=CC=C1).Reference of 4-Chloro-8-methylquinoline. Through the article, more information about this compound (cas:18436-73-2) is conveyed.
Kinetic data for the reaction of 6- and 8-alkyl-substituted 4-chloroquinolines with piperidine in four different solvents and with NaOMe in MeOH were obtained and compared. The tert-butyl group located at the position peri to the aza group is found to cause rate-depressing effects and significant increases in the energy and entropy of activation when the solvent is hydroxylic (methanol) whereas only minor changes are observed in aprotic or poor proton-donor solvents (toluene, HCONMe2, and piperidine). The results are interpreted in terms of steric inhibition of specific solvation (H bonding). 15 references.
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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia