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

Thermodynamic characteristics of electrophilic substitution reactions in 1-methyltetrazole and 1 H -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...

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Bibliographic Details
Published in:Russian chemical bulletin 2016-07, Vol.65 (7), p.1716-1721
Main Authors: Chuvylkin, N. D., Subbotin, A. N., Belen’kii, L. I.
Format: Article
Language:English
Subjects:
Aqueous solutions
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Continuum modeling
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Heterocyclic compounds
Inorganic Chemistry
Organic Chemistry
Quantum chemistry
Solvation
Substitution reactions
Tetrazoles
Thermodynamics
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Summary:Thermodynamic characteristics of electrophilic substitution reactions in 1-methyltetrazole and 1 H -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 1 H -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.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-016-1500-2