Fragmentations of 1,2-diethoxyethane by electron impact.

Yanagisawa, Tamae; Tobita, Seiji; Tajima, Susumu; Yoshifuji, Masaaki; Inamoto, Naoki

doi:10.5702/massspec.37.229

J. Mass Spectrom. Soc. Jpn.

1989

DOI: 10.5702/massspec.37.229

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Fragmentations of 1,2-diethoxyethane by electron impact.

Tamae Yanagisawa

Seiji Tobita

Susumu Tajima

et al.

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“…To date, the majority of gas-phase ion studies concerning functional group interactions have involved the interpretation of fragmentation patterns of openshell ions formed by conventional electron ionization [22][23][24][25][26][27][28][29] or the evaluation of the dissociation of closedshell ions generated by simple proton transfer reactions [30][31][32][33][34][35][36][37]. Few studies of the effects of functional groups on more complex ion-molecule or dissociation reactions have been reported.…”

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An investigation of site-selective gas-phase reactions of amino alcohols with dimethyl ether ions

Eichmann

Brodbelt

1993

J. Am. Soc. Mass Spectrom.

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The reactions of dimethyl ether ions with neutral amino alcohols were examined in both a quadrupole ion trap mass spectrometer and a triple quadrupole mass spectrometer. These ion-molecule reactions produced two types of ions: the protonated species [M+l](+) and a more complex product at [M+13](+). The abundance of the [M+13](+) ions relative to that of the [M+1](+) ions decreases with increasing formal interfunctional distance. Multistage collision-activated dissociation techniques were used to characterize the [M+13](+) product ions, their reactivities, and the mechanisms for their formation and dissociation. In addition, molecular semiempirical calculation methods were used to probe the thermochemistry of these reactions. Reaction at the amino alcohol nitrogen site is favored, and the resulting [M+13](+) addition products may cyclize for additional stabilization. Comparisons were made among the behavior of related compounds, such as alcohols, diols, amines, and diamines. The alcohols reacted only to form the protonated species, but the diols, amines, and diamines all formed significant amounts of [M+13](+) ions or related dissociation products.

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mentioning

confidence: 99%

An investigation of site-selective gas-phase reactions of amino alcohols with dimethyl ether ions

Eichmann

Brodbelt

1993

J. Am. Soc. Mass Spectrom.

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Fragmentation processes of 1,2‐diphenoxyethane and 2‐phenoxyethanol by electron impact

Sekiguchi

Ayuzawa

Fujishige

et al. 1995

Rapid Comm Mass Spectrometry

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The unimolecular fragmentation processes of 1,Zdiphenoxyethane (1) and 2-phenoxyethanol (2) upon electron impact were investigated by a combination of mass-analyzed ion kinetic energy (MIKE) spectrometry, deuterium-labelling, high resolution mass spectrometry, and kinetic energy release (KER) measurement. The MIKE spectrum and the KER measurement indicate that the predominant fragment ion at mlz 120 was generated from metastable 1+' ions via loss of a phenol molecule (C&I@, 7), and that it has the same structure as the molecular ion of 2,3-dihydrobenzofuran (C&@, 3). The metastable 2" ion eliminates C2H40 and C2H30 to produce product ions at m/z 94 (C&O+., 7") and 95 (C,@Hp+) with single and double hydrogen atom transfer, respctively . These reactions occur through some complex rearrangement reactions.Fragmentation processes of gaseous organic ions produced by electron impact have been studied extensively by a combination of mass-analyzed ion kinetic energy (MIKE) spectrometry, deuterium-labelling, and kinetic energy release (KER) measurement.' By using these techniques, we have investigated the fragmentations of some aliphatic diethers of ethylenegly~ol.~,~ In these compounds, aldehyde andlor alcohol molecules were eliminated with single hydrogen atom migration.Recently, the detailed fragmentation mechanisms of some aliphatic ethers of ethyleneglycol have been reported by Milliet et al. The fragmentation of ethyleneglycol itself has also been studied by several authors.5-' In order to rationalize these fragmentation processes, very complex rearrangement reactions have been p r~p o s e d .~-~ The reactivity and fragmentation of ethyleneglycol diethers and some a,o-dialkoxyalkanes have also been investigated by using an ion cyclotron resonance (ICR) cell9 and collision-induced dissociation (CID) spectra."To the authors' knowledge, however, little is known concerning the fragmentation of the aromatic ethers of ethylenegly~ol."-'~ In this paper we report the results of a MIKE spectometry/D-labellinglhigh resolution mass spectrometry/KER measurement study of the fragmentation pathways of 1 ,Zdiphenoxyethane (1) and 2-phenoxyethanol (2). These compounds are the simplest aromatic ethers of ethyleneglycol. EXPERIMENTALThe mass spectra and high resolution data were obtained with a Hitachi (Tokyo, Japan) M-80A doublefocusing mass spectrometer. The MIKE spectra were recorded on a Hitachi RMU-7M reversed geometry instrument. The KER values were calculated from the width at half-height of the metastable peak, after correction for the main beam.'"'' 1,2-Diphenoxyethane-l, 1 ,2,2-d4 (l-d4) and phenyl vinyl ether (4) were synthesized by the Williamson method." 2-Phenoxyethanol-1 ,l-d2 (2-d2) was obtained by reduction of methylphenoxy acetate with LiAlD4. 2-Phenoxyethanol-0-d, (2-d,) and 2-phenoxyethanol-1,1,O-d, (2-d,) were obtained by repeated treatment of the parent compounds (2 and 2-d,) with D 2 0 . The degree of labelling obtained was better than 94%. 1,2-Diphenoxyethane (l), 2,3-dihydrobenzofuran (3), styrene oxide (S), a...

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Fragmentations of 1,2-diethoxyethane by electron impact.

Cited by 2 publications

References 0 publications

An investigation of site-selective gas-phase reactions of amino alcohols with dimethyl ether ions

An investigation of site-selective gas-phase reactions of amino alcohols with dimethyl ether ions

Fragmentation processes of 1,2‐diphenoxyethane and 2‐phenoxyethanol by electron impact

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