The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Some propionitrile derivatives》. Authors are Moureu, Charles; Brown, Ralph l..The article about the compound:2-Bromopropanenitrilecas:19481-82-4,SMILESS:CC(Br)C#N).Application of 19481-82-4. Through the article, more information about this compound (cas:19481-82-4) is conveyed.
cf. Moureu, Ann. chim. phys.[7] 2, 191(1894). HOCH2CH2CN (A), b15, 110°, is obtained from CH2ClCH2OH and NaCN solution in 86% yield (C. A. 11, 2333). CH2:CHCN (B), b, 78°, is obtained in 9 g. yield from 25 g. A and 90 g. P2O5, mixed with 90 g. dry sand and distilled in vacuo. CH2BrCHBrCN, b22 106-107 °, obtained from B and the theoretical weight of Br2, d420 2.174, d420 2.140, n dD20.2 1.5452, mol. reference 31.46 (calculated 31.56), irritating to the mucous membrane. CH2BrCH2CN, colorless liquid, b25 92°, obtained from B by. adding the theoretical amount of dry HBr, d40 1.6452, d2020 1.6152, n420 1.4770, mol. reference 23.44 (calculated 23.69). Hydrolyzed with aqueous HBr (d. 1.5) the compound yielded CH2BrCH2CO2H, m. 61-2°. Treated with excess of dry HBr the nitrile yielded a white solid, m. 55-7 °, presumably CH2BrCH2CN-HBr. MeCHBr.CN, colorless liquid, b24 59°, slightly irritating to the mucous membrane, prepared by dehydration of MeCHBrCONH2 with 1.2 parts by weight of P2O5 by distilling under reduced pressure and at 250° (crude yield, 85-90%), do 1.5808, d420 1.5505, dD20 1.4585, mol. reference 23.61 (calculated 23.69). With dry HBr, the nitrile formed MeCHBrCN.HBr, m. 64-5 ° [Ann. 142, 65(1867)],. which on hydrolysis yielded (MCH- BrCO)2NH, m. 148-9°, HBr and NH4Br.
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