Massenspektrometrie instabiler organischer Moleküle, I. Ionisationspotential und Bildungsenthalpie von Dehydrobenzol

Grützmacher, Hans‐Friedrich; Lohmann, Joachim

doi:10.1002/jlac.19677050110

Cited by 42 publications

(10 citation statements)

References 17 publications

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“…l), in good agreement wit11 the value obtained by Gruetzmacher 8: Lohmaniz [3] ( d H f x P ( 1 ) = 118 & 5 kcal/mole) from electron impact studies, especially if one allows for the slight underestimation of strain energies by the MINDO/Z-method ill]. We have also calculated AHf, assuming the benzene-like structure suggested in [2], with the C-C bond lengths taken as 1.383 A, the value obtained by minimizing the energy of benzene with the MINDO/Z-method.…”

supporting

confidence: 88%

“…While their results concerning the electronic structure of I are valuable, their calculated heat of formation d H f (I) = 72.6 kcal/mole is in serious disagreement with an estimate obtained from inass spectrometric studies [3] (OHPXP Table 1. M I N D 0 / 2 and ab-initio results [2] for the heat of formation (AHf) and first ionization potential (IP) for benzene and I , 2- (I) = 118 & 5 kcal/mole, /3], tab.…”

mentioning

confidence: 85%

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Theoretical Study of the Structure and the Physico Chemical Properties of 1,2‐Benzyne

Haselbach

1971

Helvetica Chimica Acta

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IJne estimation du taux de fragmentation montrc qu'i 70 cV, 60 i 65% des ions butyle form& dans la source se dkcomposent avant de parvenir sur le collecteur. L'importance de cettc fraction ne dCpend que t r k peu de la structure originale des ions C4H,+. 1 . Theoretical Study of the Structure and the Physic0 Chemical Properties of 1,2-BenzyneSummary. The structure of 1,2-benzyne (I) has been optimized with respect to its total molecular energy using the MINDOjZ SCF-procedure. The results indicate a bond length of -1.26 A for the strained triple bond. The overall geometry suggests that I possesses considerable resonance energy. The calculated heat of formation (dHf(1) = 107 kcal/mole) is in good agrecincnt with an estimate from mass spectrometric studies (AHfexP(I) = 118 & 5 kcal/mole). From model calcula-

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confidence: 88%

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confidence: 85%

Theoretical Study of the Structure and the Physico Chemical Properties of 1,2‐Benzyne

Haselbach

1971

Helvetica Chimica Acta

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“…Although the furan adduct 6 was isolated in only 0.1% yield, these experiments demonstrated the existence of free benzyne with a lifetime of at least 20 ms under the reaction conditions. FVP of compound 10 was used later by Grützmacher [34] to obtain the mass spectrum and an approximate ionization potential of benzyne (or most likely a ring-opened C 6 H…”

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confidence: 99%

The Benzyne Story

Wentrup¹

2010

Aust. J. Chem.

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The history of o-benzyne from its early beginnings as an unobservable reactive intermediate until its present status as a very well characterized but still theoretically challenging molecule with important applications in synthesis is reviewed. The m- and p-benzynes, tridehydrobenzenes, and benzdiynes are also known, and p-benzyne is a key intermediate in the action of a potent class of ene-diyne anti-tumour compounds.

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“…In the mass spectra of various phosphines (1, 13) biphenylene ion formation is observed, but arises via a different mechanism than the formation of (C6F4),+ ' ions. Biphenylene ions are also found in the spectrum of 2,2'-diiododiphenyl mercury (14), but these are obviously due to the presence of halogen atoms.…”

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confidence: 99%

Fragmentation and rearrangement processes in the mass spectra of perhalogenoaromatic compounds. Part II. Pentafluorophenyl derivatives of GroupIV

Miller¹

1969

Can. J. Chem.

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The mass spectra of compounds of the type (C6F5)4M (M = Si, Ge, Sn, and Pb) have been studied. Bond forming rearrangements were detected, involving fluorine abstraction by the central atom, forming perfluorophenylene ions and neutral metal fluoride species. The heavier metals give simpler spectra and fragmentation schemes. The bulk of the ion current is carried by fluorocarbon ions for the silicon derivative and by organometallic or metal fluoride ions in the other three cases, SnF+ and PbF+ forming the base peaks in their spectra. When M is carbon in the compounds (CGF5)3COH and (CGFS)ZCO, there is little evidence for rearrangements and transfer of fluorine to the central carbon atom.Canadian Journal of Chemistry, 47, 1613 (1969) IntroductionThe mass spectra of some pentafluorophenyl derivatives of phosphorus, germanium, silicon, and phosphido-bridged iron carbonyls were shown to exhibit not only normal fragmentation, but also molecular rearrangements involving elimination of central atom-fluoride species formed by fluorine transfer, leaving perfluorophenylene type ions (1). King (2a,b) and Bruce (2c) also have established, by metastable ion analysis, the formation of neutral metal fluorides in mass suectra of a series of a h h a t i c and aromatic fluorocarbon derivatives of iron and cobalt. Similar results are also reported for manganese derivatives (3). Cave11 and Dobbie have reported on fragmentations and rearrangements for a series of trifluoromethyl derivatives of arsenic (4, 7) and phosphorus (5-7).In this paper the mass spectra of pentafluorophenyl derivatives of Group IV elements are discussed along with postulated mechanisms for the observed rearrangements.

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Massenspektrometrie instabiler organischer Moleküle, I. Ionisationspotential und Bildungsenthalpie von Dehydrobenzol

Cited by 42 publications

References 17 publications

Theoretical Study of the Structure and the Physico Chemical Properties of 1,2‐Benzyne

Theoretical Study of the Structure and the Physico Chemical Properties of 1,2‐Benzyne

The Benzyne Story

Fragmentation and rearrangement processes in the mass spectra of perhalogenoaromatic compounds. Part II. Pentafluorophenyl derivatives of GroupIV

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