Quantum chemical studies of azoles 7. N-alkyl substituent effect on calculated thermodynamic parameters of the electrophilic substitution mechanism in 1H-tetrazole via elimination–addition scheme without preceding formation of N-protonated azolium salts

Abstract

Thermodynamic characteristics of electrophilic substitution reactions in 1-methyltetrazole and 1H-tetrazole via the elimination–addition scheme (HO^– anion and hydroxonium ion as model agents) were compared by analysis of the quantum chemical calculation results performed using the DFT/B3LYP/6-31G(d,p) method taking into account specific solvation effects. The possibility for both reactions to occur without the preceding formation of N-protonated azolium salts was shown. This possibility has earlier been demonstrated for 1H-tetrazole using the DFT/B3LYP/6-31G(d,p) and DFT/B3LYP/6-31G(2df,p) methods taking into account the solvation effects in an aqueous solution in terms of polarized continuum model when proton was chosen as a model electrophile.