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Quantum chemical studies of azoles 9. Tetrazole halogenation according to the elimination—addition scheme without preliminary formation of N-protonated azolium salts

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Abstract

Thermodynamic characteristics of electrophilic substitution reactions of 1H-tetrazole and 2H-tetrazole proceeding by the elimination—addition scheme with F+, Cl+, and Br+ as model cations were compared using the results of DFT/B3LYP/6-31G(d,p) quantum chemical calculations carried out with inclusion of specific solvation effects. Possible reasons for lower reactivity (based on the results of calculations) of 2H-tetrazole compared to that of 1H-isomer are discussed.

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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

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  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 O. M. Nefedov on the occasion of his 85th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2578—2582, November, 2016.

For Part 8, see Ref. 1.

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Belen’kii, L.I., Subbotin, A.N. & Chuvylkin, N.D. Quantum chemical studies of azoles 9. Tetrazole halogenation according to the elimination—addition scheme without preliminary formation of N-protonated azolium salts. Russ Chem Bull 65, 2578–2582 (2016). https://doi.org/10.1007/s11172-016-1621-7

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  • DOI: https://doi.org/10.1007/s11172-016-1621-7

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