Unexpected hydrodefluorination of 3-Cl-tetrafluoropyridine. Interpretation through analysis of the potential energy surface for its radical anion Full article
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Journal of Fluorine Chemistry
ISSN: 0022-1139 |
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| Output data | Year: 2020, Volume: 234, Article number : UNSP 109513, Pages count : DOI: 10.1016/j.jfluchem.2020.109513 | ||
| Tags | Reductive dehalogenation; Reaction mechanism; Mixed fluoro-chloro-pyridines; Intermediate radical anions; Solvent reorganization; Potential energy surface sections | ||
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Abstract:
The mechanism of the reductive dehalogenation of 3-chloro-2,4,5,6-tetrafluoropyridine has been considered in terms of quantum-chemical analysis of the potential energy surface (PES) for its daughter radical anion (RA). We analyzed PES sections along the coordinates of the RA fragmentation through the loss of a halide ion. Based on DFT calculations, a model has been built that included the solvent reorganization during the RA decomposition. The model enabled us to describe the change of the RA decay channel with an increase in solvent polarity which was found by V.P. Krasnov and V.E. Platonov, 2000. The change is due to a difference in the fine mechanisms of C-F and C-Cl bond cleavage.
Cite:
Andreev R.V.
, Beregovaya I.V.
, Shchegoleva L.N.
Unexpected hydrodefluorination of 3-Cl-tetrafluoropyridine. Interpretation through analysis of the potential energy surface for its radical anion
Journal of Fluorine Chemistry. 2020. V.234. UNSP 109513 . DOI: 10.1016/j.jfluchem.2020.109513 WOS Scopus РИНЦ OpenAlex
Unexpected hydrodefluorination of 3-Cl-tetrafluoropyridine. Interpretation through analysis of the potential energy surface for its radical anion
Journal of Fluorine Chemistry. 2020. V.234. UNSP 109513 . DOI: 10.1016/j.jfluchem.2020.109513 WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | Jun 1, 2020 |
Identifiers:
| Web of science: | WOS:000535980200004 |
| Scopus: | 2-s2.0-85081932667 |
| Elibrary: | 43254412 |
| OpenAlex: | W3012411052 |