QUANTUM-CHEMICAL INVESTIGATION OF CERTAIN PHYSICOCHEMICAL PROPERTIES OF C-NITRO-1,2,3-TRIAZOLE AND N-ALKYL-4(5)-NITRO-1,2,3-TRIAZOLES

Abstract

Quantum-chemical calculations have been carried  out on molecular electrostatic potentials, proton affinity in the gas phase, gas phase basicity, and pKBH+ 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.

How to Cite
Ivashkevich, O. A.; Matulis, V. E.; Gaponik, P. N.; Sukhanov, G. T.; Filippova,  J. V.; Sukhanova, A. G.  Chem. Heterocycl. Compd. 2008, 44, 1472. [Khim. Geterotsikl. Soedin. 2008, 1816.]

For this article in the English edition see DOI 10.1007/s10593-009-0210-1