Correlation of mass spectra with structure in aromatic oxygenated compounds.Aromatic alcohols and phenols

Aczel, T.; Lumpkin, H. E.

doi:10.1021/ac50153a035

Cited by 91 publications

(17 citation statements)

References 8 publications

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“…Formation of the product ion at m/z 456 from the precursor ion indicates the first water loss. However, the second water loss from m/z 456 was not observed, suggesting the hydroxylation of the aromatic ring . Other product ions observed in the MS/MS spectrum (Figure S1e, supporting information) were m/z 429, 411, 272, 258, 243, 203, 211, 183 and m/z 70 (Scheme S3, supporting information).…”

Section: Resultsmentioning

confidence: 98%

“…loss was observed in ESI mode. This suggests that hydroxylation might occur at the aromatic ring . The formation of a high‐abundance characteristic fragment ion at m/z 211 indicates dehydrogenation at the aliphatic chain.…”

Section: Resultsmentioning

confidence: 99%

“…This suggests that hydroxylation might occur at the aromatic ring. 28 The formation of a high-abundance characteristic fragment ion at m/z 211 indicates dehydrogenation at the aliphatic chain. All these data are consistent with the structure (E)-5-(4-(4-(5-cyano-6-hydroxy-1H-…”

Section: M2 ([M + H] + M/z 456)mentioning

confidence: 99%

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Identification and characterization of vilazodone metabolites in rats and microsomes by ultrahigh‐performance liquid chromatography/quadrupole time‐of‐flight tandem mass spectrometry

Chavan

Kalariya

Tiwari

et al. 2017

Rapid Comm Mass Spectrometry

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

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Identification and characterization of vilazodone metabolites in rats and microsomes by ultrahigh‐performance liquid chromatography/quadrupole time‐of‐flight tandem mass spectrometry

Chavan

Kalariya

Tiwari

et al. 2017

Rapid Comm Mass Spectrometry

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“…After reduction of the hydroperoxides of the very weak acid fraction, the derived alcohols were examined by GC-MS, revealing a series of compounds differing by -CH2 units (mol wt 162,176,190, and 204). The fragmentation patterns of these alcohols suggested that they were methylated benzylic alcohols (11); moderately strong molecular ions, weaker M -1 ions, and strong M -15, M -17, and M -18 fragments were observed. A likely partial structure for the alcohol series is 1; the implication would be that the original hydroperoxides were methyl-substituted derivatives of l-hydroperoxy-1,2,3,4-tetrahydronaphthalene (tetralin hydroperoxide).…”

Section: Resultsmentioning

confidence: 96%

Photooxidation products of a fuel oil and their antimicrobial activity

Larson¹,

Bott²,

Hunt³

et al. 1979

Environ. Sci. Technol.

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H Photooxidation products of a no. 2 fuel oil were fractionated and examined by gas chromatography-mass spectrometry. Among the compound types identified were hydroperoxides (alkylated derivatives of tetralin hydroperoxide), phenolic compounds (highly alkylated phenols and tetrahydronaphthols), and carboxylic acids (substituted benzoic and naphthoic acids). Oil fractions and pure compounds characteristic of the photooxidation products were tested for toxicity to a yeast and several filamentous algae. 'The species tested varied in their tolerance toward the photoproducts, but hydroperoxides generally showed the highest toxicity: tetralin hydroperoxide, a t 4 X lo-,-' M. significantly reduced yeast growth. Carboxylic acids had less activity and phenolics were still less active. Tetralin hydroperoxide, a t concentrations greater than 8 X l W 5 M. reduced photosynthetic carbon fixation by Vaucht'ria and increased excretion of fixed car hon.It has been suggested that aging or weathering of petroleum surface films might lessen their toxicity to aquatic organisms because of the evaporation of toxic, low-boiling hydrocarbons (1 ) or transformation of hydrocarbons into oxygenated derivatives easily leached from slicks (2). However, thermal treatment or long-wavelength ultra\Violet (UV) irradiation of some petroleum products affords water-soluble fractions with greatly increased toxicity to bacteria (Y), algae ( 4 ) , marine invertebrates, and fish ( 5 ) . A preliminary study of the photooxidation of a no. 2 fuel oil showed that hydroperoxides, carbonyl compounds, phenols, and acids were produced ( 6 ) . Some photoproducts (hydroperoxides in particular) displayed considerable toxicity to a yeast. Succhciromyces cerecisiae. We report additional work on the molecular identification and antimicrobial activity of some constituents of the acidic fraction of the no. 2 fuel oil photoproducts. This fraction includes hydroperoxides (very weak acids having pK, = 12), phenols (weak acids, pK, = lo), and carboxylic acids (pK;, 3.51. MatcJrials arid MethodsSeparation of Acidic Fractions. The characteristics of the no. 2 fuel oil and the conditions for its irradiation with a Pyrex-filtered mercury arc were reported previously ( 6 ) . Irradiated oil (25 mL) was extracted three times with twice its volume of 1 M KOH containing 6% NaCi. T h e combined aqueous layers were washed with hexane, brought to pH 11.0, and reextracted with diethyl ether to afford a n ether-soluble "very weak acid fraction". The p H of the residual water layer was adjusted successively to 7.0 and 4.0 and extracted similarly a t each p H to afford a "weak acid" and a "strong acid" fraction, respectively.The concentrated ether extracts were separated by preparative TLC (the very weak acid fraction was first treated with thiacyclopentane ( 7 ) to convert hydroperoxides to alcohols) and the constituents of the principal bands were examined by GC-MS using a double-focusing instrument (Shrader Laboratories, Detroit, Mich.).Preparation of Water Extracts. The no. 2 fuel oil...

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“…benzylic cleavage 44,45 . This cleavage, which often dominates over or suppresses completely the dissociation pathway leading to the loss of HNC, can prevail regardless of the position of the alkyl substituent.…”

Section: F Alkylanilinesmentioning

confidence: 99%

Mass Spectrometry and Gas‐Phase Chemistry of Anilines

Eberlin

Augusti

2009

Patai's Chemistry of Functional Groups

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Introduction Ionization Energies ( IE ) and Proton Affinities ( PA ) of Anilines: The Influence of the Substituents 70 e V EI Mass Spectrometry of Anilines: The Influence of the Nature of Substituents on Unimolecular Dissociation Ortho Effects in Substituted Anilines Miscellaneous Dissociations of Ionized Anilines Chemical Ionization and Electrospray Ionization Mass Spectrometry of Anilines Gas‐Phase Reactivity of Anilines Acknowledgments

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Correlation of mass spectra with structure in aromatic oxygenated compounds.Aromatic alcohols and phenols

Cited by 91 publications

References 8 publications

Identification and characterization of vilazodone metabolites in rats and microsomes by ultrahigh‐performance liquid chromatography/quadrupole time‐of‐flight tandem mass spectrometry

Identification and characterization of vilazodone metabolites in rats and microsomes by ultrahigh‐performance liquid chromatography/quadrupole time‐of‐flight tandem mass spectrometry

Photooxidation products of a fuel oil and their antimicrobial activity

Mass Spectrometry and Gas‐Phase Chemistry of Anilines

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