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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

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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.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow, 119991, Russian Federation

    N. D. Chuvylkin, A. N. Subbotin & L. I. Belen’kii

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  1. N. D. Chuvylkin
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  2. A. N. Subbotin
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  3. L. I. Belen’kii
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Correspondence to N. D. Chuvylkin.

Additional information

For Part 6, see Ref. 1.

Based on the materials of the International Congress on the Heterocyclic Chemistry “KOST-2015” (October 18–23, 2015, Moscow, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1716–1721, July, 2016.

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Chuvylkin, N.D., Subbotin, A.N. & Belen’kii, L.I. 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. Russ Chem Bull 65, 1716–1721 (2016). https://doi.org/10.1007/s11172-016-1500-2

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  • DOI: https://doi.org/10.1007/s11172-016-1500-2

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