Ammoniakverlust aus α,ω‐Alkandiaminen im Massenspektrometer. 22. Mitteilung über das massenspektrometrische Verhalten von Stickstoffverbindungen

Mayerl, Friedrich; Hesse, Manfred

doi:10.1002/hlca.19760590113

Cited by 21 publications

(13 citation statements)

References 12 publications

(2 reference statements)

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“…The [M Ϫ NH 3 ] ؒϩ ions generated from 1,4-diaminobutane and 1,5diaminopentane react with dimethyl disulfide, but the absence of ؒ SCH 3 abstraction contradicts a previous suggestion of a distonic ion structure. 19 Additionally, CID experiments indicated that the radical cations had acyclic structures, in contrast to previous proposals. 19 Reaction of CH 5 ϩ with diamines led to the formation of cyclic [M ϩ H Ϫ NH 3 ] ؒϩ (Scheme 1).…”

Section: B Radical Cation Reactionsmentioning

confidence: 73%

“…19 Additionally, CID experiments indicated that the radical cations had acyclic structures, in contrast to previous proposals. 19 Reaction of CH 5 ϩ with diamines led to the formation of cyclic [M ϩ H Ϫ NH 3 ] ؒϩ (Scheme 1). 18 Similar results were obtained by Bouchoux et al, 20 who found that protonated amino alcohols undergo intramolecular nucleophilic substitution upon activation.…”

Section: B Radical Cation Reactionsmentioning

confidence: 73%

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12 Organic gas-phase ion chemistry

Munsch

Wenthold

2003

Annu. Rep. Prog. Chem., Sect. B

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Gas-phase ion chemistry is a useful approach for the investigation of physical organic chemistry and the study of reactivity, structure, and thermochemical properties of ionic and neutral organic substrates. This review summarizes the physical organic chemistry studies utilizing gas-phase ion chemistry reported in the past year. Among the more significant advances reported in the past year included a report of the reactivity of p-benzyne by Kenttämaa and co-workers, 1 a comparison of the S N 2 reaction in the gas-phase and in solution by Brauman and co-workers, 2 and a full characterization of the structure and energetics of cyanocarbene. 3,4 Information learned from these gas-phase ion studies includes: 1) p-benzyne undergoes radical reactions but also reacts as a weak electrophile; 2) unlike what is found in solution, steric bulk does not significantly affect the barriers for S N 2 reactions of halogenated nitriles; and 3) HCCN is a "floppy" molecule with a triplet ground state and a singlet excited state that is ca. 50 kJ mol Ϫ1 higher in energy.Papers included in this review were selected by considering contributions to the standard organic, physical, and mass spectrometry journals. The selected articles are those that address the issue of reactivity and structure of organic molecules. Our emphasis in this work is on the chemistry that is observed, and information regarding the instrumental technique is only provided in situations where it is critical for understanding the results. The majority of the studies were carried out by using Fourier transform-ion cyclotron resonance (FT-ICR), quadrupole ion trap, or flowing afterglow techniques. We have generally not included papers regarding ionization fragmentation patterns, unless the work was part of broader studies. Studies of organometallic ions were generally not included if the chemistry was dominated by the metal center. Moreover, computational studies were also not included unless they provided significant insight into specific experimental results.It was with some trepidation that we restrict the number of biological studies included in this paper. Recent advances in mass spectrometric capabilities have led to numerous fundamental studies of the properties of biologically relevant molecules. In this work, we generally have only included the studies of the simplest biological molecules, amino acids, nucleic acids, and monosaccharides. It is clear that many more future mass spectrometric studies will likely involve biological substrates. As such, it is anticipated that future versions of this report may need to be expanded to include more biologically relevant material.The articles summarized in this review are organized into broad classifications: 420

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Section: B Radical Cation Reactionsmentioning

confidence: 73%

Section: B Radical Cation Reactionsmentioning

confidence: 73%

12 Organic gas-phase ion chemistry

Munsch

Wenthold

2003

Annu. Rep. Prog. Chem., Sect. B

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“…One can also suppose that different molecular ions behave differently with regard to the exchange of the hydrogen atoms of the amino groups prior to the fragmentation. EXPERIMENTAL 1,6-Diamimhexane-l,1 ,6,6-d4 (2). Dimethyladipate was reduced in tetrahydrofuran by LiAlD4 in 1,6-hexanediol-1,1,6,6-d4 (60% yield).…”

Section: Resultsmentioning

confidence: 99%

A study of the electron impact‐induced fragmentation of 1,6‐diaminohexane

Blac

Singy

Buchs

1976

Org. Mass Spectrom.

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“…Within the same cooperation many years later the elimination of ammonia from the molecular ions of 1,4‐diaminobutane and 1,5‐diamino‐pentane was studied using collision‐induced dissociation and ion/molecule reactions, the latter being performed with use of the Bruker FTICR mass spectrometer mentioned in Subsection VII B . The motivation was that the $[{\rm M} - {\rm NH}_3 ]^{ + \bullet }$ ion from 1,4‐diaminobutane had been suggested to be the interesting ring‐closed α‐distonic ion of pyrrolidine (Mayerl & Hesse, 1976). However, the $[{\rm M} - {\rm NH}_3 ]^{ + \bullet }$ ion from neither 1,4‐diaminobutane nor 1,5‐diaminopentane behaved like a distonic ion in reactions with dimethyl disulfide (Fernandes et al, 2002), known to be an excellent substrate to identify distonic ion structures by a unique ${\rm CH}_3 {\rm S}^ \bullet $ abstraction (Stirk, Kiminkinen, & Kenttämaa, 1992).…”

Section: The Years Of Reversed Geometry Double Focusing Hybridmentioning

confidence: 99%

Four decades of joy in mass spectrometry

Nibbering

2006

Mass Spectrometry Reviews

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Tremendous developments in mass spectrometry have taken place in the last 40 years. This holds for both the science and the instrumental revolutions in this field. In chemistry the research was heavily focused on organic molecules that upon electron ionization fragmented via complex mechanistic pathways as shown by isotopic labeling experiments. These studies, including ion structure determinations, were performed with use of double focusing mass spectrometers of both conventional and reversed geometry, and equipped with various types of metastable ion scanning and collision-induced dissociation techniques developed by physical and analytical chemists. Time-resolved mass spectrometry by use of the field ionization kinetics method, developed by physical chemists, was another powerful way to unravel details of unimolecular gas phase ion dissociations. Then the development of new ionization methods, such as desorption chemical ionization, field desorption, and fast atom bombardment permitted not only to analyze unvolatile, thermally labile and higher molecular weight compounds, but also to study their chemical behavior in the gas phase, initially with use of double focusing instruments and later on with multisector and hybrid mass spectrometers. These ionization methods also enabled to study organometallic compounds and increasingly the field of medium-sized to large biomolecules, the latter being exploded in the last decade by the development of electrospray- and matrix-assisted laser desorption ionization/time-of-flight mass spectrometry. Another area of research concerned the bimolecular chemistry of organic ions with organic molecules in the gas phase. Initially this was performed with use of among others drift-cell ion cyclotron resonance spectroscopy, that later on was replaced by the developed method of ion trapping and Fourier transform ion cyclotron resonance. Combination of the latter with the afore-mentioned ionization methods has shifted also in this case the research on organic molecules to organometallic/inorganic systems, and predominantly to biomolecules in the last decade. This invited review will describe the research efforts made by the author's group over the last 40 years together with some personal experiences during his career.

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Ammoniakverlust aus α,ω‐Alkandiaminen im Massenspektrometer. 22. Mitteilung über das massenspektrometrische Verhalten von Stickstoffverbindungen

Cited by 21 publications

References 12 publications

12 Organic gas-phase ion chemistry

12 Organic gas-phase ion chemistry

A study of the electron impact‐induced fragmentation of 1,6‐diaminohexane

Four decades of joy in mass spectrometry

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