The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Benzothiazole. I. Nitration and bromination of 2-chlorobenzothiazole》. Authors are Colonna, Martino.The article about the compound:2-Chloro-6-nitrobenzo[d]thiazolecas:2407-11-6,SMILESS:O=[N+](C1=CC=C2N=C(Cl)SC2=C1)[O-]).SDS of cas: 2407-11-6. Through the article, more information about this compound (cas:2407-11-6) is conveyed.
According to the hypothesis of Bonino (C.A. 34, 323.6) direct “”cationoid”” substitution (halogenation, nitration, etc.) of benzothiazole (I) should be directed toward the positions of the H atoms statistically pos., i. e., 4 or 6, while “”anionoid”” substitution (e. g., with NaNH2, NH2OH, etc.) should be directed toward the positions of the H atom statistically neg., i. e., 2. In order to test these predictions, 2-chlorobenzothiazole (II) was prepared (cf. Ger. pat. 516,996 (C.A. 25, 3015)) by the action of PCl5 and POCl3 on 2-mercaptobenzothiazole (III). II dissolved in concentrated H2SO4, treated with EtNO3 at 0°, gives a crystalline precipitate of 2-chloro-6-nitrobenzothiazole (IV), m. 192°, which at 140° (under pressure) with alc. NH3 gives 2-amino-6-nitrobenzothiazole (V), yellow, m. 245° (alc.), identical with the compound obtained by treating p-nitro-aniline with NH4CNS (cf. Kauffmann, C.A. 29, 2660.1). IV with Br in CHCl3 gives 2-chloro-6-bromobenzothiazole, white, m. 100-1°, and the same compound is obtained by treating the diazo derivative of IV with Cu2Br2. The structure of I according to Bonino shows the pyridine-like character of the N atom, and the strictly aromatic character of the benzene nucleus; however, in this nucleus the tricentered bond is fixed, while in other nuclei it is of an oscillating type, as in the equilibrium of quinoline: (VI)⇌ (VII).
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Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI