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Quantum chemical studies of azoles 4. A novel elimination–addition mechanism of tetrazole and 1,2,4-triazole electrophilic substitution

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Abstract

Thermodynamic parameters of the addition–elimination and elimination–addition electrophilic substitution reactions of 1H-tetrazole and 1,2,4-1H-triazole obtained from DFT B3LYP/ 6-31G(d,p) quantum chemical calculations with proton as model electrophile are compared. According to calculations, the elimination–addition reactions can proceed without preliminary formation of N-protonated azolium salts.

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Authors and Affiliations

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

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

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

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Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on the occasion of his 80th birthday.

For Part 3, see Ref. 1.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2050–2054, September, 2015.

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Belen’kii, L.I., Subbotin, A.N. & Chuvylkin, N.D. Quantum chemical studies of azoles 4. A novel elimination–addition mechanism of tetrazole and 1,2,4-triazole electrophilic substitution. Russ Chem Bull 64, 2050–2054 (2015). https://doi.org/10.1007/s11172-015-1116-y

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  • DOI: https://doi.org/10.1007/s11172-015-1116-y

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