Chem Asian J 2021 Apr 12. Epub 2021 Apr 12.
Saint Petersburg State University, Department of Chemistry, Universitetsky Pr., 26, 198504, Saint Petersburg, RUSSIAN FEDERATION.
An interplay between 4-bromo- and 4-iodo-5-nitrophthalonitriles (XNPN, X = Br or I) and any one of the azines (pyridine 1 , 4-dimethylaminopyridine 2 , isoquinoline 3 , 4-cyanopyridine 4 , 2-methylpyridine 5 , 2-aminopyridine 6 , quinoline 7 , 1-methylisoquinoline 8 , and 2,2'-bipyridine 9 ) proceeds differently depending on steric and electronic effects of the heterocycles. Sterically unhindered azines 1 - 3 underwent the N -arylation to give the corresponding azinium salts (characterized by 1 H and 13 C{H} NMR and high-resolution ESI-MS). In contrast, azines 4 - 9 with sterically hindered N atoms or bearing an electron-withdrawing substituent, are formed stable co-crystals with XNPN, where two interacting molecules are bound by halogen bonding. Read More