Quantum-chemical calculations have been carried out on molecular electrostatic potentials, proton affinity in the gas phase, gas phase basicity, and pK BH+ values in aqueous solution for C-nitro- and N-alkyl-4(5)-nitro-1,2,3-triazoles, and the relative stability of the isomeric N-alkyl-4(5)-nitrotriazoles (alkyl = Me, Et, i-Pr, t-Bu) in the gas phase and in aqueous solution. For all the studied substances in the gas phase the 2H-tautomer and the N(2)-isomers were considerably more stable than the corresponding N(1) compounds, and the 3H-tautomer and N(3)-isomer were the least stable. In aqueous solution 1- and 3-isomers had close values of energies, but in the case of C-nitro-1,2,3-triazole the 1H form became even more stable than the 2H-form. It was established which ring nitrogen atoms of 1,2,3-triazoles are protonated in the gas phase and in solution. The obtained data correlate well with the results of experimental investigations on the alkylation of 1,2,3-triazoles in acidic and basic media and of the experimental investigation on the alkylation of C-nitro-1,2,3-triazoles with diethyl sulfate carried out in the present work.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1816–1828, December, 2008.
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Ivashkevich, O.A., Matulis, V.E., Gaponik, P.N. et al. Quantum-chemical investigation of certain physicochemical properties of C-nitro-1,2,3-triazole and N-alkyl-4(5)-nitro-1,2,3-triazoles. Chem Heterocycl Comp 44, 1472–1482 (2008). https://doi.org/10.1007/s10593-009-0210-1
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DOI: https://doi.org/10.1007/s10593-009-0210-1