Electron Ionization Mass Spectra of 2- and 4-Chloro- and Bromo-Substituted Diphenylamines

Rezk, A. M. Hassan; Sife-Eldeen, Kh. A.; Rabbih, M. A.; Selim, Ezzat T. M.

doi:10.1255/ejms.468

Cited by 3 publications

(1 citation statement)

References 6 publications

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“…8 The electron ionization mass spectra of 2-and 4-chlorodiphenylamine and 2and 4-bromodiphenylamine induced us to record the electron ionization mass spectra of these four compounds in order to investigate their fragmentation patterns. 9 Single-stage collision-induced dissociation (CID) on either quadrupole time-of-flight (Q-ToF) MS [10][11][12] or Fourier transform ion cyclotron resonance (FT-ICR) MS 13 was developed and applied to structural investigation. The constraints of CID MS/MS may be overcome by multistage mass spectrometry (MS n ), a procedure that offers superior control of the dissociation process, better understanding of the ion fragmentation pathways and the possibility to isolate and sequence resulting product ions until the molecule structure is unequivocally determined.…”

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confidence: 99%

Analysis of Methyl-, Chloro-, Bromo- and Trifluoromethyl-Substituted 1,9-Diphenyl-9H-Fluorene and its Isomers by Gas Chromatography-Ion Trap Multistage Tandem Mass Spectrometry

Guo

Wei

et al. 2012

Eur J Mass Spectrom (Chichester)

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This work presents a modified method to analyze methyL-, chloro-, bromo- and trifluoromethyl-substituted 1,9-diphenyt-9H-fluorene and their isomers by ion trap mass spectrometry with electron impact ionization (EI). Since MS spectra of 1,9-diphenyl-9H-fluorene with these four groups and their isomers are similar, it is difficult to distinguish them from its isomers. Multistage tandem mass spectrometry analysis involves selecting molecular ions obtained in MS spectra as precursor ions in the MS/MS process, and the fragment [C25H17]+ (m/z 317) obtained in MS/MS spectra as a precursor ion in MS3 processes. Collision-induced dissociation (CID) experiments at different activation energies were done to elucidate possible fragmentation pathways. Proposed fragmentation pathways including m/z 317 and structures of the product ions are acquired simultaneously. At a higher CID voltage, the isomers of C25H17-F3 can be distinguished in MS/MS, while the isomers of C25H17-CH3, C25H17-Cl and C25H17-Br can be distinguished in MS3. This work can provide new and valuable information needed for unambiguous characterization of such substances in complex sample matrices.

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Section: Introductionmentioning

confidence: 99%

Analysis of Methyl-, Chloro-, Bromo- and Trifluoromethyl-Substituted 1,9-Diphenyl-9H-Fluorene and its Isomers by Gas Chromatography-Ion Trap Multistage Tandem Mass Spectrometry

Guo

Wei

et al. 2012

Eur J Mass Spectrom (Chichester)

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Current literature in mass spectrometry

2002

J. Mass Spectrom.

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In order to keep subscribers up‐to‐date with the latest developments in their field, John Wiley & Sons are providing a current awareness service in each issue of the journal. The bibliography contains newly published material in the field of mass spectrometry. Each bibliography is divided into 11 sections: 1 Books, Reviews & Symposia; 2 Instrumental Techniques & Methods; 3 Gas Phase Ion Chemistry; 4 Biology/Biochemistry: Amino Acids, Peptides & Proteins; Carbohydrates; Lipids; Nucleic Acids; 5 Pharmacology/Toxicology; 6 Natural Products; 7 Analysis of Organic Compounds; 8 Analysis of Inorganics/Organometallics; 9 Surface Analysis; 10 Environmental Analysis; 11 Elemental Analysis. Within each section, articles are listed in alphabetical order with respect to author (5 Weeks journals ‐ Search completed at 1st. May. 2002)

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Electron ionization mass spectrometric study of isomeric cyclohexyl-N-phenylanilines

et al. 2011

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Electron ionization mass spectra of N-, 2-, 3-, and 4-cyclohexyl-N-phenylaniline isomers have been obtained and investigated. Molecular ions of the 2-4 isomers are the base peaks demonstrating their high stability relative to the N-isomer in which the molecular ion intensity is about 76%. The characteristic primary fragmentation pattern for each isomer is proposed and discussed. Further fragmentations of some of the primary fragment ions is also discussed.Introduction. N-cyclohexyl-N-phenylaniline (1) has been previously prepared by conventional organic synthesis [1][2][3][4][5][6]. This compound has some important applications as an anticoagulant [1] and for the stabilization of phosphorus trichloride [2]. It has also been used as an organic photoconductor for low-contrast electrophotography and for the preparation of highly photoconducting and hole injecting/hole transporting polymeric materials [4].It has been found by one of us [7] that this compound together with its other regiomers, namely, 2-, 3-, and 4-cyclohexyl-N-phenylaniline (2, 3, and 4, respectively), can be obtained by the γ-radiolysis of N-phenylaniline solutions in cyclohexane.In a previous paper we described the fragmentation patterns of 2-and 4-chloro-and bromo-substituted Nphenylanilines [8]. It was found that the spectra of these halogenated N-phenylanilines are characterized by strong molecular ion signals and two primary fragmentations of significance, including the expulsion of the halogen substituents X and HX from these four compounds. In continuation of this work, the EI mass spectra as well as the fragmentation patterns of the four isomers of cyclohexyl-N-phenylaniline, prepared as indicated earlier [7], are investigated using GC/MS. To the best of our knowledge, the mass spectra of all these compounds have not yet been published. In addition, the 2-4 isomers are new compounds, the synthesis of which has not yet been reported.Experimental. Cyclohexyl-N-phenylaniline isomers were prepared by the Co

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Electron Ionization Mass Spectra of 2- and 4-Chloro- and Bromo-Substituted Diphenylamines

Cited by 3 publications

References 6 publications

Analysis of Methyl-, Chloro-, Bromo- and Trifluoromethyl-Substituted 1,9-Diphenyl-9H-Fluorene and its Isomers by Gas Chromatography-Ion Trap Multistage Tandem Mass Spectrometry

Analysis of Methyl-, Chloro-, Bromo- and Trifluoromethyl-Substituted 1,9-Diphenyl-9H-Fluorene and its Isomers by Gas Chromatography-Ion Trap Multistage Tandem Mass Spectrometry

Current literature in mass spectrometry

Electron ionization mass spectrometric study of isomeric cyclohexyl-N-phenylanilines

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