Intramolecular hydrogen transfer in mass spectra. I. Rearrangements in aliphatic hydrocarbons and aromatic compounds

Bursey, Joan T.; Bursey, Maurice M.; Kingston, David G. I.

doi:10.1021/cr60283a001

Cited by 167 publications

(57 citation statements)

References 77 publications

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“…This ortho effect is therefore of great value for structural elucidation and has been studied mechanistically in great detail 53,54 . The structural assignment is, however, not always unequivocal and comparison with the spectra of all isomers is normally required.…”

Section: Ortho Effects In Substituted Anilinesmentioning

confidence: 99%

Mass Spectrometry and Gas‐Phase Chemistry of Anilines

Eberlin

Augusti

2009

Patai's Chemistry of Functional Groups

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Introduction Ionization Energies ( IE ) and Proton Affinities ( PA ) of Anilines: The Influence of the Substituents 70 e V EI Mass Spectrometry of Anilines: The Influence of the Nature of Substituents on Unimolecular Dissociation Ortho Effects in Substituted Anilines Miscellaneous Dissociations of Ionized Anilines Chemical Ionization and Electrospray Ionization Mass Spectrometry of Anilines Gas‐Phase Reactivity of Anilines Acknowledgments

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Section: Ortho Effects In Substituted Anilinesmentioning

confidence: 99%

Mass Spectrometry and Gas‐Phase Chemistry of Anilines

Eberlin

Augusti

2009

Patai's Chemistry of Functional Groups

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“…(i) The [MH]+ ions of phenol (2) give only a very weak peak due to loss of 28 mass units either in the ion source (Fig. l(b)), or in the field-free region ( Fig.…”

Section: Identity Of Neutral Speciesmentioning

confidence: 99%

The Claisen rearrangement of protonated allyl phenyl ether

Kingston

Beynon

Liehr

et al. 1985

Org. Mass Spectrom.

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Molecular protonated ions of ally1 phenyl ether undergo a Claisen rearrangement both in the ion source and along the flight path. The rearranged ions undergo fragmentation, the predominant loss being ethene, and only a small contribution from loss of carbon monoxide is observed. Collision-indoced dissociation spectra are used to verify the structures of the daughter ions. These spectra, together with other evidence of an acid-induced ortho rearrangement, allow a mechanism to be proposed for the ethene loss. In contrast, molecular protonated ions of propargyl phenyl ether lose exclusively carbon monoxide.

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“…The results show interesting structural and energetics effects on the product distributions obtained and provide further evidence that ring expansion to a symmetrical structure does not occur in the chemical ionization of these halogensubstituted toluenes. The evidence concerning the possible role of ring expansion in the EI fragmentation of these halogen-substituted toluenes is conflicting and has been reviewed recently (4).…”

Section: Introductionmentioning

confidence: 99%

Structural and energetics effects in the chemical ionization of halogen-substituted benzenes and toluenes

Leung¹,

Harrison²

1976

Can. J. Chem.

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HEI-WUN EEUNG and ALEX 6. HARRISON. Can. J. Chem. 54, 3439 (1976). The HZ, Dz, CH4, and CD4 chemical ionization (CI) mass spectra of XC6H5, C6H5CHzX, and XC6H4CH3 (X = Clr Br, and I) have been determined. For the benzyl halides the dominant ion observed in all CI spectra is the m / q 91 (benzyl) ion formed by loss of HX(DX) from the protonated (deuteronated) molecule. The CI spectra of the isomeric halotoluenes differ substantially from the spectra of the benzyl halides indicating that isomerization to a common (tropylium-like) structure does not occur in CI. In the H2 CI of XC6H4Y (Y = H or CH3) the major fragment ions observed are YC6H5.HC, Yc6H5f, and YC6H4+, with the relative yields depending strongly on the halogen substituent. Neither the YC6H5 .H+ ion, resulting from HX loss from the H3+.XC6H4Y complex, nor the YC6H4+ ion, resulting from HX loss from XC6H4Y .H+, are observed when X = I. On the other hand YC6H5+, resulting from elimination of X. from XC6H4Y.H+, is observed only for X = Br and I. In the CH4 CI of XC6H4Y, in addition to XC6)I4Y.Ht ions, CH3C6H4Y .H+ ions (HX loss from the CH5+.XC6H4Y complex) are observed for X = F and C1, while YC6H5t ions (loss of X'from XC6H4Y.H+) are observed only when X = I. In addition, displacement of I' by C2H5+, and by C3H5+, is observed in the CH4 CI of the iodo-substituted compounds. The dependency of the products observed and their relative yields on the identity of the halogen substituent is discussed in relation to the reaction energetics.

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Intramolecular hydrogen transfer in mass spectra. I. Rearrangements in aliphatic hydrocarbons and aromatic compounds

Cited by 167 publications

References 77 publications

Mass Spectrometry and Gas‐Phase Chemistry of Anilines

Mass Spectrometry and Gas‐Phase Chemistry of Anilines

The Claisen rearrangement of protonated allyl phenyl ether

Structural and energetics effects in the chemical ionization of halogen-substituted benzenes and toluenes

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