Attachment of neutrals during tandem mass spectrometry of sulfonic acid dyes andintermediates in an ion trap

Weisz, Adrian; Andrzejewski, Denis; Fales, Henry M.; Mandelbaum, A.

doi:10.1002/jms.357

Cited by 16 publications

(13 citation statements)

References 12 publications

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“…For analysts involved in structural elucidation of uncharacterized compounds, ion‐molecule adducts in ion‐trap mass spectrometers are a nuisance 3, 25. In this respect, it is vital to recognize at a very early stage whether an observed ion in a CID spectrum is a true fragment or an ‘artifact’ originating from an adduct with a background molecule.…”

Section: Resultsmentioning

confidence: 99%

An unexpected ion‐molecule adduct in negative‐ion collision‐induced decomposition ion‐trap mass spectra of halogenated benzoic acids

Attygalle

Kharbatia

Bialecki

et al. 2006

Rapid Comm Mass Spectrometry

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The ion observed at m/z 145 when product ion spectra of iodobenzoate anions are recorded using ion-trap mass spectrometers corresponds to the adduct ion [I(H(2)O)](-). The elements of water required for the formation of this adduct do not originate from the precursor ion but from traces of moisture present in the helium buffer gas. A collision-induced decomposition (CID) spectrum recorded from the [M-H](-) ion (m/z 251) derived from 3-iodo[2,4,5,6-(2)H(4)]benzoic acid also showed an ion at m/z 145. This observation confirmed that the m/z 145 is not a product ion resulting from a direct neutral loss from the carboxylate anion. (79)Bromobenzoate anions produce similar results showing an ion at m/z 97 for [(79)Br(H(2)O)](-). The ion-molecule reaction observed here is unique to ion-trap mass spectrometers since a corresponding ion was not observed under our experimental conditions in spectra recorded with in-space tandem mass spectrometers such as triple quadrupole or quadrupole time-of-flight instruments.

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Section: Resultsmentioning

confidence: 99%

An unexpected ion‐molecule adduct in negative‐ion collision‐induced decomposition ion‐trap mass spectra of halogenated benzoic acids

Attygalle

Kharbatia

Bialecki

et al. 2006

Rapid Comm Mass Spectrometry

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“…[24] Crystal violet degradation in solutions and/or on a paper sheet was examined by using LDI [25] and MALDI MS. [23][24][25] For the separation of products of ageing processes, thin-layer chromatography, [29] capillary zone electrophoresis or micellar electrokinetic chromatography [30] were proposed. HPLC procedures followed by MS with electrospray ionization [31][32][33][34][35][36][37][38][39][40] and atmospheric pressure chemical ionization [31,[41][42][43] have been developed mainly for analytical control of foodstuffs or examination of photo catalytic degradation of synthetic dyes in polluted waters.…”

Section: Introductionmentioning

confidence: 99%

Early synthetic dyes – a challenge for tandem mass spectrometry

et al. 2013

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The present study concerns identification of early yellow synthetic dyes from silk fibers taken from the 1930 spring color palette of the Lyon Dyers' Guild (La Chambre Syndicale des Teinturiers). The identification was based mainly on the electrospray ionization tandem mass spectrometry spectra obtained in the positive and negative ion modes. This technique was combined with high-performance liquid chromatography, which enabled separation of the analyzed compounds. Spectra registered for each of the examined synthetic dye allowed identification of their lost fragments. Moreover, isotopic profiles and exact measurements of m/z by using time of flight analyzer made possible to evaluate their elemental composition. In consequence, all obtained data, including UV-vis spectra, allowed to reconstruct molecular structures of examined colorants. Due to the lack of standards, the identification of the dyes was based only on the registration of fragment and quasi-molecular ions, what is rather uncommon in such analysis and means groping for the correct structure rather than proving signal identity by comparison with standards. Depending on substituents present in dye molecules, the lost fragments of the examined compounds involved SO(2), NO(•), NO(2)(•), CH(4), C(2)H(4), C(2)H(5)(•), C(2)H(6), CH(2)=N-CH(3), (CH(3))(2)NH, CH(2)= NH, CH(3)-NH(2), as well as CO and CO(2). The performed study led to identification of various colorants: rhodamine 6 G, rhodamine B, malachite green, quinoline yellow, picric acid and acetoquinone yellow 5JZ.

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“…The HRMS provided the elemental composition of the isolated isomers. Structural assignment of the QY disulfonated positional isomers by various mass spectrometric techniques was previously reported [25,26]. Assignments of most of the proton NMR signals in the di- and trisulfonated compounds were relatively straightforward.…”

Section: Resultsmentioning

confidence: 97%

Preparative separation of di- and trisulfonated components of Quinoline Yellow using affinity-ligand pH-zone-refining counter-current chromatography

Weisz

Mazzola

Ito

2009

Journal of Chromatography A

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Four positionally isomeric 2-(2-quinolinyl)-1H-indene-1,3(2H)-dionedisulfonic acids (SA) and one triSA, components of the color additive Quinoline Yellow (QY, Color Index No. 47005), were isolated from the dye mixture by affinity-ligand pH-zone-refining counter-current chromatography (CCC) through complementary use of ion-exchange and ion-pair reagents as the ligand. The added ligands facilitated the partitioning of the very polar polysulfonated components into the organic stationary phase of the two-phase solvent systems that consisted of isoamyl alcohol-methyl tert.-butyl ether-acetonitrile-water (3:5:1:7), (3:4:1:7) or (3:1:1:5). Thus, separation of a 5 g portion of QY using sulfuric acid as the retainer and dodecylamine as the ligand (an ion-exchange reagent, 20% in the stationary phase), resulted in 1.21 g of 6′,5-diSA and 1.69 g of 6′,8′,5-triSA, both of over 99% purity. A minor component, 8′,4-diSA, not previously reported was also obtained (4.8 mg of over 94% purity) through a similar separation of a different batch of QY using hydrochloric acid as the retainer and 10% dodecylamine as the ligand in the stationary phase. Two components that co-eluted (0.55 g) in the 5 g separation were separated when trifluoroacetic acid was used as the retainer and tetrabutylammonium hydroxide (an ion-pair reagent) as the ligand. The separation resulted in 20.7 mg of 6′,4-diSA, not previously reported, and 111.8 mg of 8′,5-diSA, both of over 98% purity. The isolated compounds were characterized by high-resolution mass spectrometry and proton nuclear magnetic resonance with correlated spectroscopy assignments.

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Attachment of neutrals during tandem mass spectrometry of sulfonic acid dyes andintermediates in an ion trap

Cited by 16 publications

References 12 publications

An unexpected ion‐molecule adduct in negative‐ion collision‐induced decomposition ion‐trap mass spectra of halogenated benzoic acids

An unexpected ion‐molecule adduct in negative‐ion collision‐induced decomposition ion‐trap mass spectra of halogenated benzoic acids

Early synthetic dyes – a challenge for tandem mass spectrometry

Preparative separation of di- and trisulfonated components of Quinoline Yellow using affinity-ligand pH-zone-refining counter-current chromatography

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