Standard

Aromatic SN F-Approach to Fluorinated Phenyl tert-Butyl Nitroxides. / Tretyakov, Evgeny; Fedyushin, Pavel; Panteleeva, Elena et al.

In: Molecules, Vol. 24, No. 24, 4493, 08.12.2019.

Research output: Contribution to journal › Article › peer-review

Harvard

Tretyakov, E, Fedyushin, P, Panteleeva, E, Gurskaya, L, Rybalova, T, Bogomyakov, A, Zaytseva, E, Kazantsev, M, Shundrina, I & Ovcharenko, V 2019, 'Aromatic SN F-Approach to Fluorinated Phenyl tert-Butyl Nitroxides', Molecules, vol. 24, no. 24, 4493. https://doi.org/10.3390/molecules24244493

APA

Tretyakov, E., Fedyushin, P., Panteleeva, E., Gurskaya, L., Rybalova, T., Bogomyakov, A., Zaytseva, E., Kazantsev, M., Shundrina, I., & Ovcharenko, V. (2019). Aromatic SN F-Approach to Fluorinated Phenyl tert-Butyl Nitroxides. Molecules, 24(24), [4493]. https://doi.org/10.3390/molecules24244493

Vancouver

Tretyakov E, Fedyushin P, Panteleeva E, Gurskaya L, Rybalova T, Bogomyakov A et al. Aromatic SN F-Approach to Fluorinated Phenyl tert-Butyl Nitroxides. Molecules. 2019 Dec 8;24(24):4493. doi: 10.3390/molecules24244493

Author

Tretyakov, Evgeny ; Fedyushin, Pavel ; Panteleeva, Elena et al. / Aromatic SN F-Approach to Fluorinated Phenyl tert-Butyl Nitroxides. In: Molecules. 2019 ; Vol. 24, No. 24.

BibTeX

@article{61f1ac9281f34327a5e317e0602c205f,
title = "Aromatic SN F-Approach to Fluorinated Phenyl tert-Butyl Nitroxides",
abstract = "The interaction of octafluorotoluene (1a), as well as pentafluorobenzonitrile (1b) with tert-butylamine, followed by the oxidation of thus formed tert-butylanilines (2a,b) with meta-chloroperoxybenzoic acid led to functionalized perfluorinated phenyl tert-butyl nitroxides [namely, 4-(N-tert-butyl(oxyl)amino)heptafluorotoluene (3a) and 4-(N-tert-butyl(oxyl)amino)tetrafluorobenzonitrile (3b)] with nearly quantitative total yields. The molecular and crystal structures of nitroxide 3a were proved by single crystal X-ray diffraction analysis. The radical nature of both nitroxides was confirmed by ESR data. The interaction of Cu(hfac)2 with the obtained nitroxides 3a,b gave corresponding transbis(1,1,1,5,5,5-hexafluoropentane-2,4-dionato-κ2O,O0)bis{4-(N-tert-butyl(oxyl)amino)perfluoroareneκO}copper (II) complexes ([Cu(hfac)2(3a)2] and [Cu(hfac)2(3b)2]). X-ray crystal structure analysis showed square bipyramid coordination of a centrally symmetric Cu polyhedron with the axial positions occupied by oxygen atoms of the nitroxide groups. Magnetic measurements revealed intramolecular ferromagnetic exchange interactions between unpaired electrons of Cu(II) ions and paramagnetic ligands, with exchange interaction parameters JCu–R reaching 53 cm−1 ",
keywords = "Aromatic nucleophilic substitution, Copper-nitroxide complexes, Fluoroarenes, Magneto-structural correlations, Nitroxides, Tert-butylanilines, magneto-structural correlations, MECHANISM, tert-butylanilines, COPPER(II), COMPLEXES, aromatic nucleophilic substitution, nitroxides, HYDROGEN-BONDS, fluoroarenes, TRANSITION, NITRONYL NITROXIDE, FERROMAGNETIC INTERACTIONS, RADICALS, MAGNETIC-PROPERTIES, EXCHANGE, copper-nitroxide complexes, Crystallography, X-Ray, Coordination Complexes/chemistry, Oxygen/chemistry, Copper/chemistry, Molecular Structure, Oxidation-Reduction, Halogenation, Ligands, Fluorocarbons/chemistry",
author = "Evgeny Tretyakov and Pavel Fedyushin and Elena Panteleeva and Larisa Gurskaya and Tatyana Rybalova and Artem Bogomyakov and Elena Zaytseva and Maxim Kazantsev and Inna Shundrina and Victor Ovcharenko",
note = "Publisher Copyright: {\textcopyright} 2019 by the authors.",
year = "2019",
month = dec,
day = "8",
doi = "10.3390/molecules24244493",
language = "English",
volume = "24",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "24",

}

RIS

TY - JOUR

T1 - Aromatic SN F-Approach to Fluorinated Phenyl tert-Butyl Nitroxides

AU - Tretyakov, Evgeny

AU - Fedyushin, Pavel

AU - Panteleeva, Elena

AU - Gurskaya, Larisa

AU - Rybalova, Tatyana

AU - Bogomyakov, Artem

AU - Zaytseva, Elena

AU - Kazantsev, Maxim

AU - Shundrina, Inna

AU - Ovcharenko, Victor

N1 - Publisher Copyright: © 2019 by the authors.

PY - 2019/12/8

Y1 - 2019/12/8

N2 - The interaction of octafluorotoluene (1a), as well as pentafluorobenzonitrile (1b) with tert-butylamine, followed by the oxidation of thus formed tert-butylanilines (2a,b) with meta-chloroperoxybenzoic acid led to functionalized perfluorinated phenyl tert-butyl nitroxides [namely, 4-(N-tert-butyl(oxyl)amino)heptafluorotoluene (3a) and 4-(N-tert-butyl(oxyl)amino)tetrafluorobenzonitrile (3b)] with nearly quantitative total yields. The molecular and crystal structures of nitroxide 3a were proved by single crystal X-ray diffraction analysis. The radical nature of both nitroxides was confirmed by ESR data. The interaction of Cu(hfac)2 with the obtained nitroxides 3a,b gave corresponding transbis(1,1,1,5,5,5-hexafluoropentane-2,4-dionato-κ2O,O0)bis{4-(N-tert-butyl(oxyl)amino)perfluoroareneκO}copper (II) complexes ([Cu(hfac)2(3a)2] and [Cu(hfac)2(3b)2]). X-ray crystal structure analysis showed square bipyramid coordination of a centrally symmetric Cu polyhedron with the axial positions occupied by oxygen atoms of the nitroxide groups. Magnetic measurements revealed intramolecular ferromagnetic exchange interactions between unpaired electrons of Cu(II) ions and paramagnetic ligands, with exchange interaction parameters JCu–R reaching 53 cm−1

AB - The interaction of octafluorotoluene (1a), as well as pentafluorobenzonitrile (1b) with tert-butylamine, followed by the oxidation of thus formed tert-butylanilines (2a,b) with meta-chloroperoxybenzoic acid led to functionalized perfluorinated phenyl tert-butyl nitroxides [namely, 4-(N-tert-butyl(oxyl)amino)heptafluorotoluene (3a) and 4-(N-tert-butyl(oxyl)amino)tetrafluorobenzonitrile (3b)] with nearly quantitative total yields. The molecular and crystal structures of nitroxide 3a were proved by single crystal X-ray diffraction analysis. The radical nature of both nitroxides was confirmed by ESR data. The interaction of Cu(hfac)2 with the obtained nitroxides 3a,b gave corresponding transbis(1,1,1,5,5,5-hexafluoropentane-2,4-dionato-κ2O,O0)bis{4-(N-tert-butyl(oxyl)amino)perfluoroareneκO}copper (II) complexes ([Cu(hfac)2(3a)2] and [Cu(hfac)2(3b)2]). X-ray crystal structure analysis showed square bipyramid coordination of a centrally symmetric Cu polyhedron with the axial positions occupied by oxygen atoms of the nitroxide groups. Magnetic measurements revealed intramolecular ferromagnetic exchange interactions between unpaired electrons of Cu(II) ions and paramagnetic ligands, with exchange interaction parameters JCu–R reaching 53 cm−1

KW - Aromatic nucleophilic substitution

KW - Copper-nitroxide complexes

KW - Fluoroarenes

KW - Magneto-structural correlations

KW - Nitroxides

KW - Tert-butylanilines

KW - magneto-structural correlations

KW - MECHANISM

KW - tert-butylanilines

KW - COPPER(II)

KW - COMPLEXES

KW - aromatic nucleophilic substitution

KW - nitroxides

KW - HYDROGEN-BONDS

KW - fluoroarenes

KW - TRANSITION

KW - NITRONYL NITROXIDE

KW - FERROMAGNETIC INTERACTIONS

KW - RADICALS

KW - MAGNETIC-PROPERTIES

KW - EXCHANGE

KW - copper-nitroxide complexes

KW - Crystallography, X-Ray

KW - Coordination Complexes/chemistry

KW - Oxygen/chemistry

KW - Copper/chemistry

KW - Molecular Structure

KW - Oxidation-Reduction

KW - Halogenation

KW - Ligands

KW - Fluorocarbons/chemistry

UR - http://www.scopus.com/inward/record.url?scp=85076381618&partnerID=8YFLogxK

U2 - 10.3390/molecules24244493

DO - 10.3390/molecules24244493

M3 - Article

C2 - 31817965

AN - SCOPUS:85076381618

VL - 24

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 24

M1 - 4493

ER -

ID: 22980718