FORMATION MECHANISM OF 1,3-bis(2-OXOPROPYL)-3Н-1,2,3-BENZOTRIAZOLIUM TRIIODIDE IN THE ALKYLATION REACTION OF 1,2,3-BENZOTRIAZOLE WITH 1-IODOPROPAN-2-ONE
V. A. Shagun, I. A. Dorofeev, L. G. Shagun
1A. E. Favorsky Irkutsk Institute of Chemistry, Russian Academy of Sciences, Irkutsk
2A. E. Favorsky Irkutsk Institute of Chemistry, Russian Academy of Sciences
Keywords: quantum chemical calculation, ionic liquid, reaction mechanism, alkylation, 1,2,3-benzotriazole, 1-iodopropan-2-one
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)-3Н-1,2,3-benzotriazolium triiodide is studied. A mechanism consisting of four steps (N-1-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)-3Н-1,2,3-benzotriazolium) is proposed. Thermodynamic and kinetic parameters of these steps are obtained.
|
