The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Conformation of biaryls. Dipole moment measurements of o-methylbiphenyls》. Authors are Sato, Takeo.The article about the compound:2-Methylglutaronitrilecas:4553-62-2,SMILESS:N#CC(C)CCC#N).Application In Synthesis of 2-Methylglutaronitrile. Through the article, more information about this compound (cas:4553-62-2) is conveyed.
cf. CA 54, 19584a. 5,5′-Dinitro- (I), 5,5′-dichloro-2,2′-dimethylbiphenyl (II), and 2-methyl-3′,5-dinitrobiphenyl (III) were prepared, their dipole moments measured and the interplanar angles calculated The results for I and II showed the rings to be nearly perpendicular to each other, whereas III showed a slight trans arrangement with inclined C6H6 rings at an angle of 76°. 2-Iodo-4-nitrotoluene (100 g.) and 150 g. dry sand heated to 215° 100 g. activated Cu-bronze (IV) added over 1 hr. with good stirring at 215-20°, heated and kept 1.5 hrs. at 250°, the mixture poured into dry sand and extracted with EtOH gave a low yield of I, yellow needles, m. 177-8° (HOAc or Me2CO). 4-Chloro-2-iodotoluene (16 g.) heated at 240-50°, 20 g. IV added over 1 hr., the mixture heated and kept 40 min. at 280-90°, extracted with Me2CO and distilled gave II, b4 140-55°, n20 1.5961. IV (15 g.) added with stirring over 30 min. to a mixture of 4 g. 2-iodo-4-nitrotoluene and 75 g. m-nitroiodobenzene at 220-30°, heated and kept 30 min. at 240-50°, extracted with Me2CO and the solvent evaporated gave III, yellow plates, m. 145-6° (EtOH).
There is still a lot of research devoted to this compound(SMILES：N#CC(C)CCC#N)Application In Synthesis of 2-Methylglutaronitrile, and with the development of science, more effects of this compound(4553-62-2) can be discovered.
Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com