Gas phase ion chemistry of para substituted benzene diazonium ions, their salt clusters and their related phenyl cations

Vrkic, Ana K.; O’Hair, Richard A. J.

doi:10.1016/s1387-3806(02)00647-4

Cited by 14 publications

(14 citation statements)

References 68 publications

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“…In establishing the fragmentation pathways and associating mass spectral fragmentation with chemical structure, it is assumed that product ions are subunits of their precursor ion. However, during the course of using ion trap-based ESI-MS/MS to characterize natural products, it has been reported earlier [9][10][11][12][13][14][15] that certain fragmentation products react with H 2 o and other commonly used ESI solvent molecules, thereby complicating MS/MS data interpretation.…”

Section: Journal Of Mass Spectrometrymentioning

confidence: 99%

Solvation in Gas-Phase Reactions of Sulfonic Groups Containing Ionic Liquids in Electrospray Ionization Quadrupole Ion Trap Mass Spectrometry

Cao

et al. 2009

Eur J Mass Spectrom (Chichester)

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In electrospray ionization (ESI) quadrupole ion trap mass spectrometry, certain fragment ions generated in the ion trap from a series of sulfonic groups containing ionic liquids (ILs) are found to undergo ion-molecule reactions with ESI solvent molecules (water, acetonitrile and methanol) to form adduct species. These unexpected solvated fragment ions severely complicate the interpretation of mass spectrometric data. Multi-stage fragmentation mass spectra were used to ascertain the chemical structures of these adduct species. It is important that solvation must be taken into account in order to prevent erroneous data interpretation for sulfonic groups containing ILs.

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Section: Journal Of Mass Spectrometrymentioning

confidence: 99%

Solvation in Gas-Phase Reactions of Sulfonic Groups Containing Ionic Liquids in Electrospray Ionization Quadrupole Ion Trap Mass Spectrometry

Cao

et al. 2009

Eur J Mass Spectrom (Chichester)

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“…The mechanisms of action for these coordination complexes are closely tied to their hydrolysis products, and these products and mechanisms are poorly understood, partly due to the possibility of multiple equilibria with similar energetics [11,12]. It is for these reasons that coordination complexes of Ni(II), Pd(II), and Pt(II) in aqueous solutions have been the focus of a number of investigations [13][14][15][16][17].Electrospray mass spectrometry (ESMS) is particularly well suited for the study of metal-containing aqueous solutions, and a variety of such studies have been conducted [18,19]. We recently reported the results of one such study into aqueous solutions of dibromo(ethylenediamine)palladium(II) [20].…”

mentioning

confidence: 99%

“…Electrospray mass spectrometry (ESMS) is particularly well suited for the study of metal-containing aqueous solutions, and a variety of such studies have been conducted [18,19]. We recently reported the results of one such study into aqueous solutions of dibromo(ethylenediamine)palladium(II) [20].…”

mentioning

confidence: 99%

Complexes of dichloro(ethylenediamine)palladium(II) observed from aqueous solutions by electrospray mass spectrometry

Bach

Green

Nagore

et al. 2007

J. Am. Soc. Mass Spectrom.

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Aqueous solutions of dichloro(ethylenediamine)palladium(II) were investigated using electrospray mass spectrometry (ESMS). The most abundant peak (m/z 436.8) was attributed to the dimeric Pd(en)Cl 2 ·Pd(en)Cl ϩ ion. We conjecture that the structures of the observed ions arise from the clustering of the hydrolysis products of the parent compound. This hypothesis was tested experimentally by carrying out a series of collision-induced dissociation (CID) experiments and deuterium exchange reactions. It was also assessed by performing density functional theory (DFT) calculations, from which optimized structures and reaction energetics were obtained. These results were compared with our earlier ESMS study of an aqueous Pd(en)Br 2 solution. Calculations were also carried out on the Pd(en)Br 2 system to facilitate the comparisons. Conclusions are drawn regarding the species present in the two aqueous solutions. (J Am Soc Mass Spectrom 2007, 18, 769 -777) © 2007 American Society for Mass Spectrometry T he last decade has seen a resurgence of interest in the coordination chemistry of transition metals. This is due in large part to their therapeutic value as antitumor agents. Many of these agents are platinum(II) complexes, the four best known being cisplatin, carboplatin, oxaliplatin, and nedaplatin [1][2][3]. Palladium(II) complexes have also attracted attention for similar reasons [4][5][6][7].In vivo, hydrolysis of these compounds occurs, and it is these hydrolytic products that yield their medicinal activity [8,9]. The hydrolytic products are also strongly linked to issues of renal toxicity [10]. The mechanisms of action for these coordination complexes are closely tied to their hydrolysis products, and these products and mechanisms are poorly understood, partly due to the possibility of multiple equilibria with similar energetics [11,12]. It is for these reasons that coordination complexes of Ni(II), Pd(II), and Pt(II) in aqueous solutions have been the focus of a number of investigations [13][14][15][16][17].Electrospray mass spectrometry (ESMS) is particularly well suited for the study of metal-containing aqueous solutions, and a variety of such studies have been conducted [18,19]. We recently reported the results of one such study into aqueous solutions of dibromo(ethylenediamine)palladium(II) [20]. When the solution was electrosprayed into a quadrupole ion-trap mass spectrometer, a number of previously unreported species were detected, the principle one being a dimeric ion formed from the Pd(en)Br 2 parent compound and the Pd(en)Br ϩ ion. The dimeric ion was subjected to collision-induced dissociation (CID), and these MS n experiments revealed a series of ions formed through the sequential loss of HBr molecules. Complexes observed from the electrospray process are not necessarily a reflection of those complexes in solution, but they may instead simply represent species in solution from which the complexes are produced in the electrospray desolvation process. This has been observed previously in solutions containi...

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“…4 In addition, they represent a suitable model for heteroaromatic diazonium ions implied in DNA base deamination. [5][6][7] The gas-phase chemistry of arenediazonium ions has been experimentally investigated via electrospray ionization of their tetrafluoroborate salts, 8 while quantum chemistry methods have been recently used to study the nucleophilic substitution of nitrogen in the benzenediazonium ion by one water molecule to form protonated phenol. 9 The structure of the benzenediazonium ion is particularly interesting.…”

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confidence: 99%

Gas‐phase synthesis and detection of the benzenediazonium ion, C₆H₅N. A joint atmospheric pressure chemical ionization and guided ion beam experiment

Guella

Ascenzi

Franceschi

et al. 2005

Rapid Comm Mass Spectrometry

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An ion of formula C6H5N 2+ (m/z 105) has been produced by atmospheric pressure chemical ionization (APCI) of benzene and clearly detected in the corresponding positive ion mass spectrum. Its elemental composition has been established by the mass shift at m/z 110 observed when measurements were carried out with hexadeuterated benzene. MS2 experiments performed in the ion‐trap analyzer, and guided ion beam (GIB) experiments on the reaction of the phenyl cation with nitrogen molecules, allow us to establish that the detected C6H5N 2+ ion is the benzenediazonium ion. To the best of our knowledge, this is the first report on the gas‐phase total synthesis of the benzenediazonium ion within the APCI source. Copyright © 2005 John Wiley & Sons, Ltd.

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Gas phase ion chemistry of para substituted benzene diazonium ions, their salt clusters and their related phenyl cations

Cited by 14 publications

References 68 publications

Solvation in Gas-Phase Reactions of Sulfonic Groups Containing Ionic Liquids in Electrospray Ionization Quadrupole Ion Trap Mass Spectrometry

Solvation in Gas-Phase Reactions of Sulfonic Groups Containing Ionic Liquids in Electrospray Ionization Quadrupole Ion Trap Mass Spectrometry

Complexes of dichloro(ethylenediamine)palladium(II) observed from aqueous solutions by electrospray mass spectrometry

Gas‐phase synthesis and detection of the benzenediazonium ion, C₆H₅N. A joint atmospheric pressure chemical ionization and guided ion beam experiment

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Gas phase ion chemistry of para substituted benzene diazonium ions, their salt clusters and their related phenyl cations

Cited by 14 publications

References 68 publications

Solvation in Gas-Phase Reactions of Sulfonic Groups Containing Ionic Liquids in Electrospray Ionization Quadrupole Ion Trap Mass Spectrometry

Solvation in Gas-Phase Reactions of Sulfonic Groups Containing Ionic Liquids in Electrospray Ionization Quadrupole Ion Trap Mass Spectrometry

Complexes of dichloro(ethylenediamine)palladium(II) observed from aqueous solutions by electrospray mass spectrometry

Gas‐phase synthesis and detection of the benzenediazonium ion, C6H5N. A joint atmospheric pressure chemical ionization and guided ion beam experiment

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Product

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Gas‐phase synthesis and detection of the benzenediazonium ion, C₆H₅N. A joint atmospheric pressure chemical ionization and guided ion beam experiment