Basicity of isomeric ditetrazolylbenzenes and their N-tert-butyl derivatives

Abstract

The basicity constants \((pK_{BH^ + } ,pK_{BH^{2 + } } )\) of 1,2-, 1,3-, and 1,4-bis(tetrazol-5-yl)benzenes and their N-tert-butyl derivatives in aqueous sulfuric acid and the dissociation constants (pKHB) of the corresponding H-complexes with p-fluorophenol in carbon tetrachloride were determined by UV and IR spectroscopy. Mono-and diprotonation of isomeric ditetrazolylbenzenes is observed in the acidity range (H0) from −1 to −5 (\(pK_{BH^ + } \) −2.5 to −3.0; \(pK_{BH^{2 + } } \) −3.8 to −4.9). Introduction of a tert-butyl group into the 2-position of the heteroring almost does not affect the basicity of ditetrazolyl benzenes. Among the examined compounds, 1,2-bis(2-tert-butyltetrazol-5-yl)benzene is the strongest proton acceptor with respect to p-fluorophenol as standard proton donor, presumably due to formation of a complex with bifurcated (three-center) hydrogen bond.