The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Nuclear-substituted derivatives of 4,4′-diaminodiphenyl sulfone》. Authors are Berg, S. S..The article about the compound:3-Bromo-4-chloronitrobenzenecas:16588-26-4,SMILESS:BrC1=C(C=CC(=C1)[N+](=O)[O-])Cl).Computed Properties of C6H3BrClNO2. Through the article, more information about this compound (cas:16588-26-4) is conveyed.
The therapeutic effect of (4-H3NC6H4)3SO3 prompted the investigation of the halogen derivatives; these were tested orally in vivo against Staphylococcus aureus and Streptococcus pyogenes in mice; a decrease in toxicity in the order Cl < Br < iodine, together with corresponding decrease in activity, was observed 2,4-Br(O2N)C6H3NH2 (18.5 g.), through the diazo reaction, gives 12.5 g. 1-chloro-2-bromo-4-nitrobenzene, b0.1 100°, m. 61°. p-O2NC6H4SH (1.55 g.) and 0.4 g. NaOH in 20 cc. EtOH, added to 1.9 g. 3,4-Cl2C6H3NO2 in 10 cc. EtOH and refluxed 2 h., give 1.3 g. 2-chloro-4,4'-dinitrodiphenyl sulfide (I), yellow, m. 144°; the 2-Br analog, yellow, m. 159°, and the 2-I analog, yellow, m. 168°. 3,4-Cl2C6H3NO2 (15 g.) in 60 cc. EtOH, treated (5 min.) with 10 g. Na2S.9H2O in 40 cc. 25% aqueous EtOH and refluxed 6 h., gives 7.2 g. [2,4-Cl(O2N)C6H3]2S, yellow, m. 163°; the portion (3 g.) insoluble in 95% AcOH is the compound C24H12O5N4Cl4S2, probably RN(→O):NR, where R = 3,4-Cl[2,4-Cl(O2N)C6H3S]C6H3S-, red, m. 195°. 2,2'-Diiodo-4,4'-dinitrodiphenyl sulfide (II), pale red, m. 186°. 2,4-Br(O2N)C6H3OH yields an acetate (III), pale yellow, m. 86°; 13 g. III, 7.8 g. p-O2NC6H4SH, 3 g. K2CO3, and 100 cc. Me2CO, refluxed 2 h., yield 6 g. 4,4'-dinitro-2-acetoxydiphenyl sulfide (IV), yellow, m. 100°. Dropwise addition of 7.5 g. KMnO4 in 50 cc. hot H2O to 10 g. I in 150 cc. boiling AcOH gives 8 g. 2-chloro-4,4'-dinitrodiphenyl sulfone (V), m. 182-3°; 2-Br analog, m. 162°, 2-I analog, pale yellow, m. 165°; the sulfone from II, yellow, m. 260°. IV yields 4,4'-dinitro-2-hydroxydiphenyl disulfone, yellow, m. 216°. Reduced Fe (10 g.), added slowly to 5 g. V in 200 cc. boiling AcOH and the mixture heated 10 min. at 90°, gives 3 g. 2-chloro-4,4'-diaminodiphenyl sulfone, pale yellow, m. 114°; 2-Br analog, yellow, m. 157°; 2-I analog, buff, m. 207°. 2,2'-Dichloro-4,4'-diaminodiphenyl sulfone, orange, m. 263°; 2,2'-di-I analog, m. 280°. 4,4'-Diamino-2-hydroxydiphenyl sulfone, m. 134-5° [sulfate, m. 208° (decomposition)] (cf. Burton and Hoggarth, C.A. 39, 4854.7). When you point to this article, it is believed that you are also very interested in this compound(16588-26-4)Computed Properties of C6H3BrClNO2 and due to space limitations, I can only present the most important information.
Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts