Electric Literature of C7H4ClN3O2. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 2-Chloro-7-nitro-1H-benzo[d]imidazole, is researched, Molecular C7H4ClN3O2, CAS is 15965-55-6, about Benzimidazoles. II. Effect of benzene nucleus substituents on the nuclopphilic reactivity of some 2-chloro-benzimidazoles. Author is Ricci, Alfredo; Vivarelli, Piero.
cf. CA 67: 64300p. An equimol. mixture of 4,2-R(H2N)C6H3NH2.2HCl, or 3,2-R(H2N)C6H3NH2.2HCl and urea, heated 20 min. at 160-80°, the reaction mixture extracted with hot 10% NaOH and the alk. solution acidified with HCl, precipitated known 5(6)-substituted- or 4(7)-substituted-2-benzimidazolones, resp., which (0.01 mole) with 0.07 mole POCl3 and a few drops of concentrated HCl, heated 3-4 hrs. at 160-70° in a sealed tube yielded the following I (R, m.p., and % yield given): 5(6)-NO2, 222-3°, -; 5(6)-Cl, 207-8°, 70; 5(6)-Me, 185-6°, 72; 5(6)-MeO, 170-1°, 40; 4(7)-NO2, 196-7°, 40; 4(7)-Cl, 187-8°, 70; 4(7)-Me, 141-2°, 50; 4(7)-MeO, 151-2°, 55. Kinetic studies on the nucleophilic reactivity of I, carried out with piperidine at 100°, indicated that the 2-Cl mobility increases when R is electron-withdrawing, and decreases when R is electron donor. A linear correlation was also found for the effect of the substituents on the reaction center with σmeta + σpara for the position 5(6) and σortho + σmeta for the 4(7)-position, resp.
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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com