The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Oxidation of guanine and guanosine by bromine》. Authors are Shapiro, Robert; Agarwal, Satish C..The article about the compound:8-Bromoguaninecas:3066-84-0,SMILESS:NC(N1)=NC(NC(Br)=N2)=C2C1=O).HPLC of Formula: 3066-84-0. Through the article, more information about this compound (cas:3066-84-0) is conveyed.
In order to establish the chem. basis for the mutagenic effect of brominating agents, guanine (I) and guanosine (II) were subjected to the action of Br, and the reaction products were investigated. Treatment of I with excess Br in H2O at room temperature for several days afforded 38% oxalylguanidine (III), m. >300°. Alternate routes to III were: (1) CrO3 oxidation of 2amino-4,6-dihydroxypyrimidine, or (2) condensation of EtO2CCO2Et with H2NC(NH2): NH.H2CO3. The latter reaction also yielded oxalylbiguanide (IV), m. 232-4°. In addition to III, the following degradation products were formed from I upon reaction with Br (method of isolation and percent yield given): oxaluric acid (NH4+ salt, 32); guanidine (picrate, 26); and oxalic acid (Ca++ salt, 24). The presence of urea was also demonstrated chromatographically and estimated spectrophotometrically. Reaction of I with Br in a limited amount of H2O gave rise to 8-bromoguanine, from which the same degradation products were produced upon further treatment with aqueous Br. When II was allowed to react with excess Br in H2O the initial product (65% yield) was identified as 8-bromoguanosine (V). Upon further reaction, V was degraded to the following products: oxalic acid, guanidine, urea, ribose, D-ribosylurea, and D-ribosyloxaluric acid. Paper chromatography and electrophoresis were used for the separation and identification of these products. The mutagenic action of Br is attributed to destruction of the guanine residues in nucleic acids. The loss of guanine would result in disruption of H bonds and a weakening of the secondary structure of the nucleic acid chains.
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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem