Interaction of Fullerenes with Organosilanes in the Ionization Chamber of a Mass Spectrometer under Electron Impact and the Reaction of C60 with Tetraphenylsilane in Solution under UV Irradiation

C60 was shown to react with organosilanes Me4Si, Ph2SiH2, Ph2MeSiH, Ph4Si, and α-naphthylphenylmethylsilane in the electron ionization ion source of a mass spectrometer with the transfer of the corresponding organic radicals (Me, Ph, and α-naphthyl) from the silanes to the fullerene. The reactions w...

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Main Authors: Yury I. Lyakhovetsky, Elena A. Shilova, Alexandra P. Pleshkova, Alexander I. Belokon, Sergey O. Yakushin, Boris L. Tumanskii
Format: Article
Language:English
Published: Wiley 2016-01-01
Series:Journal of Spectroscopy
Online Access:http://dx.doi.org/10.1155/2016/8158623
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author Yury I. Lyakhovetsky
Elena A. Shilova
Alexandra P. Pleshkova
Alexander I. Belokon
Sergey O. Yakushin
Boris L. Tumanskii
author_facet Yury I. Lyakhovetsky
Elena A. Shilova
Alexandra P. Pleshkova
Alexander I. Belokon
Sergey O. Yakushin
Boris L. Tumanskii
author_sort Yury I. Lyakhovetsky
collection DOAJ
description C60 was shown to react with organosilanes Me4Si, Ph2SiH2, Ph2MeSiH, Ph4Si, and α-naphthylphenylmethylsilane in the electron ionization ion source of a mass spectrometer with the transfer of the corresponding organic radicals (Me, Ph, and α-naphthyl) from the silanes to the fullerene. The reactions were accompanied by hydrogen addition to some products and hydrogen loss from them. C70 reacted with Me4Si analogously. A reaction mechanism involving homolytic dissociation of the silanes under electron impact to the corresponding organic radicals, which react further with C60 at the surface of the ionization chamber of the mass spectrometer to give the respective adducts, was offered. A mechanistic study of the reaction of C60 with Me4Si supported it. No silicon containing derivatives of the fullerenes were found. C60 reacted with Ph4Si in solution under UV irradiation in a similar fashion furnishing phenyl derivatives of the fullerene. These results provide an additional support to the hypothesis formulated earlier that the homolytic reactive mass spectrometry of fullerenes (the reactions of fullerenes with other species in the ionization chambers of mass spectrometers and their mass spectral monitoring) can predict the reactivity of them toward the same reagents in solution to a significant extent.
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publishDate 2016-01-01
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series Journal of Spectroscopy
spelling doaj-art-ab4213419754467ca880eb23a8122dcf2025-02-03T01:11:21ZengWileyJournal of Spectroscopy2314-49202314-49392016-01-01201610.1155/2016/81586238158623Interaction of Fullerenes with Organosilanes in the Ionization Chamber of a Mass Spectrometer under Electron Impact and the Reaction of C60 with Tetraphenylsilane in Solution under UV IrradiationYury I. Lyakhovetsky0Elena A. Shilova1Alexandra P. Pleshkova2Alexander I. Belokon3Sergey O. Yakushin4Boris L. Tumanskii5A.N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, 28 Vavilov Street, GSP-1, V-334, Moscow 119991, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, 28 Vavilov Street, GSP-1, V-334, Moscow 119991, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, 28 Vavilov Street, GSP-1, V-334, Moscow 119991, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, 28 Vavilov Street, GSP-1, V-334, Moscow 119991, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, 28 Vavilov Street, GSP-1, V-334, Moscow 119991, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, 28 Vavilov Street, GSP-1, V-334, Moscow 119991, RussiaC60 was shown to react with organosilanes Me4Si, Ph2SiH2, Ph2MeSiH, Ph4Si, and α-naphthylphenylmethylsilane in the electron ionization ion source of a mass spectrometer with the transfer of the corresponding organic radicals (Me, Ph, and α-naphthyl) from the silanes to the fullerene. The reactions were accompanied by hydrogen addition to some products and hydrogen loss from them. C70 reacted with Me4Si analogously. A reaction mechanism involving homolytic dissociation of the silanes under electron impact to the corresponding organic radicals, which react further with C60 at the surface of the ionization chamber of the mass spectrometer to give the respective adducts, was offered. A mechanistic study of the reaction of C60 with Me4Si supported it. No silicon containing derivatives of the fullerenes were found. C60 reacted with Ph4Si in solution under UV irradiation in a similar fashion furnishing phenyl derivatives of the fullerene. These results provide an additional support to the hypothesis formulated earlier that the homolytic reactive mass spectrometry of fullerenes (the reactions of fullerenes with other species in the ionization chambers of mass spectrometers and their mass spectral monitoring) can predict the reactivity of them toward the same reagents in solution to a significant extent.http://dx.doi.org/10.1155/2016/8158623
spellingShingle Yury I. Lyakhovetsky
Elena A. Shilova
Alexandra P. Pleshkova
Alexander I. Belokon
Sergey O. Yakushin
Boris L. Tumanskii
Interaction of Fullerenes with Organosilanes in the Ionization Chamber of a Mass Spectrometer under Electron Impact and the Reaction of C60 with Tetraphenylsilane in Solution under UV Irradiation
Journal of Spectroscopy
title Interaction of Fullerenes with Organosilanes in the Ionization Chamber of a Mass Spectrometer under Electron Impact and the Reaction of C60 with Tetraphenylsilane in Solution under UV Irradiation
title_full Interaction of Fullerenes with Organosilanes in the Ionization Chamber of a Mass Spectrometer under Electron Impact and the Reaction of C60 with Tetraphenylsilane in Solution under UV Irradiation
title_fullStr Interaction of Fullerenes with Organosilanes in the Ionization Chamber of a Mass Spectrometer under Electron Impact and the Reaction of C60 with Tetraphenylsilane in Solution under UV Irradiation
title_full_unstemmed Interaction of Fullerenes with Organosilanes in the Ionization Chamber of a Mass Spectrometer under Electron Impact and the Reaction of C60 with Tetraphenylsilane in Solution under UV Irradiation
title_short Interaction of Fullerenes with Organosilanes in the Ionization Chamber of a Mass Spectrometer under Electron Impact and the Reaction of C60 with Tetraphenylsilane in Solution under UV Irradiation
title_sort interaction of fullerenes with organosilanes in the ionization chamber of a mass spectrometer under electron impact and the reaction of c60 with tetraphenylsilane in solution under uv irradiation
url http://dx.doi.org/10.1155/2016/8158623
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