Generation of perfluorinated 1-alkylbenzocyclobuten-1-yl and 1-alkylindan-1-yl cations. On paradoxical stabilizing influence of an electron-withdrawing perfluoroisopropyl group on the relative stabilities of the cations Full article
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Journal of Fluorine Chemistry
ISSN: 0022-1139 |
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| Output data | Year: 2016, Volume: 192, Pages: 31-40 Pages count : 10 DOI: 10.1016/j.jfluchem.2016.10.009 | ||||
| Tags | Fluorinated; Benzocyclobutene; Indane; Perfluoroisopropyl group; Cation; DFT calculations | ||||
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Abstract:
When perfluoro-1-alkylbenzocyclobutenes and -indanes were dissolved in an excess of SbF5, perfluorinated alkylbenzocycloalken-1-yl cations containing a fluorine atom or a perfluoroallcyl group in the cationic centre were generated. Contrary to expectations, a number of stable long-lived perfluoro-1-isopropylbenzocycloalken-1-yl cations containing an electron-withdrawing perfluoroisopropyl group in the cationic centre have been obtained. The DFT (B3LYP/6-31G*) calculations showed that the relative stabilities of isomeric cations containing a fluorine atom or a perfluoroalkyl group in the cationic centre change in favor of cations containing a perfluoroalkyl group in the cationic center when going from a CF3 to a CF(CF3)(2) group. This is in accordance with the experimental data. (C) 2016 Elsevier B.V. All rights reserved.
Cite:
Mezhenkova T.V.
, Karpov V.M.
, Beregovaya I.V.
, Zonov Y.V.
, Chuikov I.P.
, Platonov V.E.
Generation of perfluorinated 1-alkylbenzocyclobuten-1-yl and 1-alkylindan-1-yl cations. On paradoxical stabilizing influence of an electron-withdrawing perfluoroisopropyl group on the relative stabilities of the cations
Journal of Fluorine Chemistry. 2016. V.192. P.31-40. DOI: 10.1016/j.jfluchem.2016.10.009 WOS Scopus РИНЦ OpenAlex
Generation of perfluorinated 1-alkylbenzocyclobuten-1-yl and 1-alkylindan-1-yl cations. On paradoxical stabilizing influence of an electron-withdrawing perfluoroisopropyl group on the relative stabilities of the cations
Journal of Fluorine Chemistry. 2016. V.192. P.31-40. DOI: 10.1016/j.jfluchem.2016.10.009 WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | Dec 1, 2016 |
Identifiers:
| Web of science: | WOS:000390073300004 |
| Scopus: | 2-s2.0-84994103529 |
| Elibrary: | 27583646 |
| OpenAlex: | W2535130790 |