Radical reactions with selected organic compounds in the gas phase

Budzikiewicz, H.; Drabner, G.

doi:10.1002/oms.1210240805

Cited by 5 publications

(1 citation statement)

References 23 publications

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“…The above observations suggest either that (1) a radical mechanism is in effect for which the kinetics and the radicals are different from previously proposed radical reactions occurring in the high-pressure chemical ionization source or (2) that a nonradical mechanism is in effect. With regard to the first point Budzikiewicz has proposed that "alleged radical reactions prior to ionization" demand further investigation (30). From his data Budzikiewicz concludes that insertion of CH" and CH2 rather than substitution by alkyl radicals such as CHa" may be the pathway for formation of many adducts observed in methane-enhanced NCI mass spectrometry.…”

Section: Resultsmentioning

confidence: 99%

Adduct ion formation in the methane-enhanced negative chemical ionization mass spectrometry of 2-(alkylthio)- and 2-alkoxy-s-triazines

Mattina¹,

Huang²,

Hayes³

1990

Anal. Chem.

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+ 25]" are observed at significant abundance In the highpressure, methane-enhanced, negative chemical Ionization (NCI) mass spectra of seven 2-(aikylthio)-s-tr1azlnes. Under the same experimental conditions an adduct ion at [ + 12]*" Is noted In the mass spectra of six 2-alkoxy-s-triazines. These adduct Ions are Interferences In the mass spectral analysis of these compounds. Detailed studies using methane-d4, ia02/CH4, and Ar as alternate NCI enhancement gases reveal that the species responsible for adduct ion formation originate from the methane gas. This was confirmed by high-resolution accurate mass measurements of the adduct ions. Colllslonally activated decomposition tandem mass spectrometry experiments were performed In an attempt to elucidate the structure of the adducts. The variation of the adduct Ion abundance as a function of sample pressure, emission current, repeUer voltage, and Ion source temperature Is also reported and possible mechanisms for the formation of the adduct Ions are examined.

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Section: Resultsmentioning

confidence: 99%

Adduct ion formation in the methane-enhanced negative chemical ionization mass spectrometry of 2-(alkylthio)- and 2-alkoxy-s-triazines

Mattina¹,

Huang²,

Hayes³

1990

Anal. Chem.

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Radical‐induced aromatic substitution between benzoyl peroxide and benzenediols in the gas phase characterized by mass spectrometry

Tu¹,

Liu²

1992

Org. Mass Spectrom.

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A radical-induced aromatic substitution mechanism for the reaction between benzoyl peroxide and benzenediols in the gas phase was characterized by mass spectrometry. The benzoyloxy radical produced from the hornolysis of benzoyl peroxide associates at its carbonyl group with the phenolic hydroxyl group. The pairing tendency of the unpaired electron on the oxygen of the radical induces electron transfer along the hydrogen bond, which results in the rupture of the 0-H bond of the phenol and aromatic substitution at the ortho position of the benzoyloxy radical. Supporting evidence for the mechanism was obtained by isotope labelling.

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Chemical ionization mass spectrometry of benzoyl peroxide: A radical aromatic substitution resulting in biphenylcarboxylic acid in the gas phase

Zou

Tang

et al. 1993

Org. Mass Spectrom.

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A radical aromatic substitution resulting in biphenylcarboxylic acid is inferred for the decomposition of benzoyl peroxide from the chemical ionization and collision-induced dissociation mass spectra. The thermolysis of benzoyl peroxide gives rise to a benzoyloxy radical, which undergoes rapid decarboxylation and hydrogen abstraction leading to phenyl radical and benzoic acid, respectively. Attack of the resulting phenyl radical on the benzoic acid results in biphenylcarboxylic acid. On the other hand, the phenyl radical abstracts a hydrogen atom to yield benzene, which is then subjected to the attack of a benzoyloxy radical, affording phenyl benzoate. This substitution reaction rather than the recombination of benzoyloxy and phenyl radicals is found to be responsible for the formation of phenyl benzoate under the present conditions.

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Radical reactions with selected organic compounds in the gas phase

Abstract: 1. FWHM ≈ 100ksub-ppmMS MS 1 CID 1 ECD 2 ETD 3 post-translational modiication; PTM ECD ETD 1 ETD ECD 1 MALDI-MS ECD/ETD Hydrogen Attachment/Abstraction Dissocia-tionHAD 4 2. 1 H ECD ETD EID 5 CTD 6 MAD 7 1 MALDI-MS ESI-MS ECD ETD MALDI MALDI in-source decay ISD

Cited by 5 publications

References 23 publications

Adduct ion formation in the methane-enhanced negative chemical ionization mass spectrometry of 2-(alkylthio)- and 2-alkoxy-s-triazines

Adduct ion formation in the methane-enhanced negative chemical ionization mass spectrometry of 2-(alkylthio)- and 2-alkoxy-s-triazines

Radical‐induced aromatic substitution between benzoyl peroxide and benzenediols in the gas phase characterized by mass spectrometry

Chemical ionization mass spectrometry of benzoyl peroxide: A radical aromatic substitution resulting in biphenylcarboxylic acid in the gas phase

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