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Formation mechanism of 1,3-bis(2-oxopropyl)-3H-1,2,3-benzotriazolium triiodide in the alkylation reaction of 1,2,3-benzotriazole with 1-iodopropan-2-one

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Abstract

Within DFT (B3LYP) methods the potential surface of the interaction between 1-iodopropan-2-one and 1,2,3-benzotriazole resulting in the formation of 1,3-bis(2-oxopropyl)-3H-1,2,3-benzotriazolium triiodide is studied. A mechanism consisting of four steps (N1-alkylation of 1,2,3-benzotriazole, elimination of molecular iodine during partial reduction of 1-iodopropan-2-one with hydrogen iodide, formation of the triiodide structure, and formation of 1,3-bis(2-oxopropyl)-3H-1,2,3-benzotriazolium) is proposed. Thermodynamic and kinetic parameters of these steps are obtained.

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Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, Russia

    V. A. Shagun, I. A. Dorofeev & L. G. Shagun

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  1. V. A. Shagun
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  2. I. A. Dorofeev
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  3. L. G. Shagun
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Correspondence to V. A. Shagun.

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Original Russian Text Copyright © 2013 by V. A. Shagun, I. A. Dorofeev, L. G. Shagun

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Translated from Zhurnal Strukturnoi Khimii, Vol. 54, No. 5, pp. 819–824, September–October, 2013.

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Shagun, V.A., Dorofeev, I.A. & Shagun, L.G. Formation mechanism of 1,3-bis(2-oxopropyl)-3H-1,2,3-benzotriazolium triiodide in the alkylation reaction of 1,2,3-benzotriazole with 1-iodopropan-2-one. J Struct Chem 54, 857–862 (2013). https://doi.org/10.1134/S0022476613050041

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  • DOI: https://doi.org/10.1134/S0022476613050041

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