Physical organosilicon chemistry. II. Mass spectral cracking patterns of phenylsilane and ortho-, meta- and para-substituted benzyl- and phenyltrimethylsilanes

Freeburger, M. E.; Hughes, B. M.; Buell, Glen R.; Tiernan, T. O.; Spialter, Leonard

doi:10.1021/jo00806a016

Cited by 19 publications

(8 citation statements)

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“…and [M2H] 2+ , respectively. These high‐resolution accurate mass data correct the erroneous assignments by previous workers2,9 for some fragment ions, proposed without accurate mass data, such as m/z 53, 54, 55, and 65.…”

Section: Resultssupporting

confidence: 61%

“…The dissociation of organosilicon ions has been studied extensively over the years 1–11. Comparison of their dissociation properties with those of their carbon analogues has been an interesting subject in mass spectrometric studies.…”

mentioning

confidence: 99%

“…have been limited 2–9. Even though it was studied in the early days of mass spectrometry,2,3 it had not received much attention since then, until a recent study of ion‐molecule reactions using ion cyclotron resonance spectrometry by Beauchamp and coworkers 4,5. It was found that the [MH] + ion is produced in two isomeric forms, non‐interconverting at room temperature, by electron ionization (EI) of phenylsilane.…”

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confidence: 99%

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Collision‐induced dissociation of the phenylsilane molecular ion

Choe

2002

Rapid Comm Mass Spectrometry

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The high-energy collision-induced dissociation of the phenylsilane molecular ion generated by electron ionization has been investigated using tandem mass spectrometry (MS/MS). It was observed that the dissociation of the molecular ion (M(+*)) occurs mainly via [M-H](+), [M-2H](+*), and [M-3H](+), followed by two consecutive losses of C(2)H(2). The structures of the precursors for the [M-CH(3)](+), [M-SiH](+), and [M-SiH(2)](+*) ions are proposed. The data suggest that the molecular ion undergoes rearrangements to several isomers prior to dissociation, including the ion containing a five-membered carbon ring. Reaction mechanisms are proposed for the dissociations via the isomeric molecular ions.

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Section: Resultssupporting

confidence: 61%

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confidence: 99%

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confidence: 99%

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Collision‐induced dissociation of the phenylsilane molecular ion

Choe

2002

Rapid Comm Mass Spectrometry

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“…From the results of recent years we will mention only certain observations of the migration of methyl 59 , methoxy-64 , phenyl 65 , and other organic 16 » 19 groups. We emphasise that the frequently observed ion of type RjE* (E = Si, Ge, Sn, or Pb) which gives an intense, and in many instances the base peak, is rearranged to a considerable extent or completely, although frequently it could formally be formed also by simple breaking of a single bond (removal of a terminal group).…”

Section: Migration Of Groupsmentioning

confidence: 99%

Mass Spectra of Organometallic Compounds of Group IVb

Orlov¹

1973

Russ. Chem. Rev.

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Characteristic features of the dissociation of ions of organometallic compounds with silicon, germanium, tin, and lead are considered. Cyclic compounds are discussed separately; results on the following aspects are surveyed: rearrangements, metastable and multiply-charged ions, products of ionic-molecular reactions, and also the mass spectra of negative ions and correlations between ion decomposition processes and the thermal decomposition of the molecules of the compounds concerned. There is a bibliography of 115 references.

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“…4 No examples are reported concerning the intramolecular interaction between a [(CH,),Si]+ group attached to an aromatic nucleus with a phenyl ring and/or oxygen-containing group.…”

Section: Introductionmentioning

confidence: 99%

The mass spectral fragmentation of 2,2′‐bis‐trimethylsilylbenzhydrylethers. An indication for transannular hydrogen/deuterium rearrangements and transannular elimination reactions

Akkerman

Evers

Kerkstra

1976

Org. Mass Spectrom.

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The mass spectra of the methyl-, trideuteromethyl-, ethyl-and pentadeuteroethylethers of 2,2'-bi~-trimethylsilylbenzhydrol are reported. The most significant ions arise from the [M -CH,]+ ion, formed by loss of a methyl radical from one of the trimethylsilyl groups. After ring formation by interaction of the siliconium ion centre with an aromatic nucleus, the ion loses (CH,),Si-OR (R = CH,, C,H,, CD, and C2Ds), giving ion m/e 223. The fragment (CH3),Si-0CH3 is also eliminated in the four ethers investigated from the ion [M -R]+. Attack of the siliconium ion centre in the [M -CH,]+ ion on the ether oxygen leads to the generation of the [(CH,),Si+OR] ion.

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Physical organosilicon chemistry. II. Mass spectral cracking patterns of phenylsilane and ortho-, meta- and para-substituted benzyl- and phenyltrimethylsilanes

Cited by 19 publications

References 1 publication

Collision‐induced dissociation of the phenylsilane molecular ion

Collision‐induced dissociation of the phenylsilane molecular ion

Mass Spectra of Organometallic Compounds of Group IVb

The mass spectral fragmentation of 2,2′‐bis‐trimethylsilylbenzhydrylethers. An indication for transannular hydrogen/deuterium rearrangements and transannular elimination reactions

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