Electron impact mass spectrometry of monocyclic and spirocyclic oxyphosphorane compounds

Chen, Xin; Zhao, Yufen; Fu, Hua; Wang, Jingzun

doi:10.1002/jms.1190300515

Cited by 2 publications

(4 citation statements)

References 4 publications

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“…The FD and EI mass spectra gave abundant odd electron ions, which was consistent with the EI mass spectrometry of oxyphosphorane. 4 The CI mass spectra showed abundant even electron ions, including protonated amino acids arising from complex rearrangements. The three kinds of mass spectrometry could complement one another.…”

Section: Resultsmentioning

confidence: 98%

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Mass spectra of pentacoordinate spirobicyclic imino(alkyl)acetoxyphosphoranes

Zhao

et al. 1997

Rapid Commun. Mass Spectrom.

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The mass spectral fragmentation pathways of pentacoordinate spirobicyclic imino(alkyl)acetoxyphosphoranes were investigated by field desorption, electron impact and chemical ionization mass spectrometry, together with the B/E linked scan technique. The three methods gave abundant characteristic fragment ion information, showing some common and different fragmentation patterns which could be useful for characterizing other spirobicyclic phosphoranes. Scheme 1. Synthetic pathway for pentacoordinate spirobicyclic 1,3,2-imino(alkyl)acetoxyphosphoranes.

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Section: Resultsmentioning

confidence: 98%

“…2,3 Their mass spectral pathways have been investigated by electron impact mass spectrometry (EIMS). 4 To our knowledge, the synthesis and mass spectral analysis of pentacoordinate spirobicyclic imino(alkyl)acetoxyphoranes has not been reported. These compounds might be important intermediates for biosynthesis of proteins.…”

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confidence: 99%

Mass spectra of pentacoordinate spirobicyclic imino(alkyl)acetoxyphosphoranes

Zhao

et al. 1997

Rapid Commun. Mass Spectrom.

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“…So far, the electrospray ionization mass spectrometric (ESI‐MS) fragmentation characteristics of some pentacoordinate phosphoranes have been studied . Quantum chemistry methods have also been used to investigate some reactions in the gas phase.…”

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confidence: 99%

“…[19,23] So far, the electrospray ionization mass spectrometric (ESI-MS) fragmentation characteristics of some pentacoordinate phosphoranes have been studied. [24][25][26] Quantum chemistry methods have also been used to investigate some reactions in the gas phase. However, the mass spectra of P-AAs containing a carboxyl-phosphoryl anhydride moiety, a phosphoramidate bond (P-N bond) and a phenanthrenequinone group have not been reported yet.…”

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Fragmentation of pentacoordinate spirobicyclic aminoacyl‐phosphoranes (P‐AAs) by electrospray ionization tandem mass spectrometry concerning P–O and P–N bond cleavage

Gao

Zhu

et al. 2011

Rapid Comm Mass Spectrometry

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The fragmentation pathways of both protonated and sodiated pentacoordinate spirobicyclic aminoacylphosphoranes (P-AAs) have been studied by electrospray ionization multi-stage mass spectrometry (ESI-MS(n)) in positive mode. The possible pathways and their mechanisms are elucidated through the combination of ESI-MS/MS, isotope ((15)N and (2)H) labeling and high-resolution Fourier transform ion cyclotron resonance (FTICR)-MS/MS. The relative Gibbs free energies (ΔG) of the product ions and possible fragmentation pathways are estimated at the B3LYP/6-31 G(d) level of theory. The theoretical calculations show that both protonated and sodiated P-AAs would quickly fragment before Berry pseudorotation. For protonated P-AAs, they have different tendencies to P-O or P-N bond cleavage. For sodiated P-AAs, the P-N bond is easier to cleave and produces the tetracoordinated phosphorus ion H. These results to some extent may give a clue to the chemistry of the active sites of phosphoryl transfer enzymes and will enrich the gas-phase ESI-MS ion chemistry of pentacoordinate phosphoranes.

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Electron impact mass spectrometry of monocyclic and spirocyclic oxyphosphorane compounds

Cited by 2 publications

References 4 publications

Mass spectra of pentacoordinate spirobicyclic imino(alkyl)acetoxyphosphoranes

Mass spectra of pentacoordinate spirobicyclic imino(alkyl)acetoxyphosphoranes

Fragmentation of pentacoordinate spirobicyclic aminoacyl‐phosphoranes (P‐AAs) by electrospray ionization tandem mass spectrometry concerning P–O and P–N bond cleavage

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