Fragmentation Mechanism of <i>Trans</i>‐α‐Aryl‐β‐enamino Esters

Jiang, Nan; Wang, Jian‐Bo; He, Md‐Yu

doi:10.1002/cjoc.20020200815

Chin. J. Chem.

2002

DOI: 10.1002/cjoc.20020200815

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Fragmentation Mechanism of Trans‐α‐Aryl‐β‐enamino Esters

Nan Jiang

Jian‐Bo Wang

Md‐Yu He

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Cited by 2 publications

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“…the mass spectral fragmentation of trans-a-aryl-b-enamino esters was reported in the literature. 25 Here we report mass spectrometric differentiation of syn and anti isomers of a-sulfanyl-b-amino acid derivatives.…”

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confidence: 98%

Differentiation of Diasteromeric α-Sulfanyl-β-Amino Acid Derivatives by Electrospray Ionisation Tandem Mass Spectrometry

Ramanjaneyulu

Darshan

Mahendar

et al. 2011

Eur J Mass Spectrom (Chichester)

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A set of diastereomeric α-sulfanyl-β-amino acid derivatives, which are important building blocks for pharmaceuticals with potent biological activity, are studied by electrospray ionization tandem mass spectrometry. The collision induced dissociation (CID) spectra of [M+H](+), [M+NH(4)](+), [M+Na](+) and [M+Li](+) of the diastereomers were studied, among them the CID of [M+Na](+) and [M+Li](+) showed consistent differences in the relative abundance of characteristic ions that enabled distinction of the anti isomers from syn isomers. The decomposition pathways for the diagnostic ions were arrived at based on high-resolution mass spectrometry data, multiple mass spectrometry data, deuterium labeling experiments and the mass shift in accordance with the substituents located at different places. Loss of (R(1)-C(6)H(4)-CH=NH) and (Cat-NH-SO(2)R(2)) from [M+Cat](+), where Cat=Na and Li, and the product ions as a results of McLafferty rearrangement involving either >S=O or >C=O group were found to be diagnostic. The McLafferty rearrangement product ions involving >S=O group were more abundant in syn isomers while those involving >C=O group were more abundant in anti isomer. The selectivity observed in the decomposition of [M+Li](+) ions was found to be similar to that of [M+Na](+) ions, but in few cases the differences are marginal in the decomposition [M+Li](+) ions.

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mentioning

confidence: 98%

Differentiation of Diasteromeric α-Sulfanyl-β-Amino Acid Derivatives by Electrospray Ionisation Tandem Mass Spectrometry

Ramanjaneyulu

Darshan

Mahendar

et al. 2011

Eur J Mass Spectrom (Chichester)

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Investigation on Mass Spectral Fragmentation Mechanism of C₂‐Symmetric Chiral Bis(oxazoline) and Bis(thiazoline)

Chen

et al. 2005

Chin. J. Chem.

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The electron impact mass spectra of ten new C 2 -symmetric chiral bis(oxazoline) and bis(thiazoline) have been studied. Bis(thiazoline) and bis(oxazoline) possess the same fragmentation mechanism under EI conditions. An unusual fragmentation pathway has been found in the compounds studied. Due to the presence of phenyl group, compounds 6 and 10 undergo a new fragmentation pathway except for the common way as the other eight compounds. Mass analyzed ion kinetic energy spectra experiments and high resolution accurate mass measurement were conducted to confirm the proposed fragmentation pathways.

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Fragmentation Mechanism of Trans‐α‐Aryl‐β‐enamino Esters

Cited by 2 publications

References 9 publications

Differentiation of Diasteromeric α-Sulfanyl-β-Amino Acid Derivatives by Electrospray Ionisation Tandem Mass Spectrometry

Differentiation of Diasteromeric α-Sulfanyl-β-Amino Acid Derivatives by Electrospray Ionisation Tandem Mass Spectrometry

Investigation on Mass Spectral Fragmentation Mechanism of C₂‐Symmetric Chiral Bis(oxazoline) and Bis(thiazoline)

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Fragmentation Mechanism of Trans‐α‐Aryl‐β‐enamino Esters

Cited by 2 publications

References 9 publications

Differentiation of Diasteromeric α-Sulfanyl-β-Amino Acid Derivatives by Electrospray Ionisation Tandem Mass Spectrometry

Differentiation of Diasteromeric α-Sulfanyl-β-Amino Acid Derivatives by Electrospray Ionisation Tandem Mass Spectrometry

Investigation on Mass Spectral Fragmentation Mechanism of C2‐Symmetric Chiral Bis(oxazoline) and Bis(thiazoline)

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Investigation on Mass Spectral Fragmentation Mechanism of C₂‐Symmetric Chiral Bis(oxazoline) and Bis(thiazoline)