Ammonia chemical ionization mass spectra of esters and amides of oxyacids of phosphorus

Cload, P.; Hutchinson, D. W.

doi:10.1002/oms.1210180204

Cited by 26 publications

(5 citation statements)

References 5 publications

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“…Protonated phosphoric acid ( m/z 99) is formed by a series of hydrogen rearrangements and losses of alkene, and was found to be the major product ion for triethyl, tri‐n‐propyl, triisobutyl, tri‐n‐butyl and the isomers of tris(chloropropyl) phosphate. The same fragmentation pathway, as reported previously for some phosphate triesters,15, 16 was found for all these compounds. For tris(2‐chlorethyl) phosphate, the m/z 223 ion formed after one single rearrangement and cleavage was predominant.…”

Section: Resultssupporting

confidence: 86%

“…positive‐ion chemical ionization (PICI), the high‐mass ions are more likely to survive the ionization and can be further dissociated in the second MS step. The fragmentation mechanisms under CID for some organophosphates ionized by PICI15, 16 and API,17 respectively, have previously been investigated. The aim of this study was to develop and evaluate a GC/PICI‐CID‐MS method in selected‐reaction monitoring (SRM) mode for organophosphate triesters in indoor air samples.…”

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confidence: 99%

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Selective determination of organophosphate flame retardants and plasticizers in indoor air by gas chromatography, positive‐ion chemical ionization and collision‐induced dissociation mass spectrometry

Björklund

Isetun

Nilsson

2004

Rapid Comm Mass Spectrometry

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Gas chromatography/ion trap mass spectrometry with in-source ionization and dissociation was used in positive-ion chemical ionization (PICI) mode for the determination of organophosphate triesters in indoor air. These compounds are widely used as additive flame retardants and plasticizers in different types of materials and have become ubiquitous pollutants in indoor environments. When using collision-induced dissociation in PICI mode the fragmentation of the organophosphate triesters can be performed in a more controllable way than in electron ionization (EI) mode. The developed selected-reaction monitoring method provided high selectivity for the investigated compounds. For 8-h air measurements (corresponding to 1.5 m3 of sampled air) the limit of detection of the method was determined to be in the range 0.1-1.4 ng m(-3), which is comparable with nitrogen-phosphorus detection and about 50-fold lower than when using EI in selected-ion monitoring mode. The presented method was applied to samples from three common indoor environments, in which a number of organophosphate triesters were identified and quantified. The dominating compound was found to be tris(2-chloropropyl) phosphate, which occurred at levels up to 0.8 microg m(-3).

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Section: Resultssupporting

confidence: 86%

mentioning

confidence: 99%

Selective determination of organophosphate flame retardants and plasticizers in indoor air by gas chromatography, positive‐ion chemical ionization and collision‐induced dissociation mass spectrometry

Björklund

Isetun

Nilsson

2004

Rapid Comm Mass Spectrometry

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“…Compound (1) was a weak Inhibitor of cell free DNA polymerases Induced by either virus straln but the concentrationp producing 50% Inhibition of the enzyme activity for either polymerase were considerably greater than that for phosphonoacetic acid (Table 2). Compounds (8)(9)(10)(11) were inactive at 4 1000 gtM (DNA polymerase assay) or 4 4 mM (plaque reduction assay). No compounds were cytotoxic at concentration 4 4 mM in the plaque reduction assay.…”

Section: Discussionmentioning

confidence: 99%

“…Alteration In the structure of (1) such as ring alkylation (4), Insertion of an additlonal methylene group between the tetrazole ring and the phosphonic acid residue (2) . or replacement of the phosphonic acid by a carboxylic acid residue (10) gave compounds which were poor chelators of zinc Ion (pKd. < 4) and which were devoid of antiviral activity.…”

Section: Discussionmentioning

confidence: 99%

The antiviral activity of tetrazole phosphonic acids and their analogues

Hutchinson

Naylor

1985

Nucl Acids Res

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5-(Phosphonomethyl)-1H-tetrazole and a number of related tetrazoles have been prepared and their effects on the replication of Herpes Simplex Viruses-1 and -2 have been investigated as well as their abilities to inhibit the DNA polymerases induced by these viruses and the RNA transcriptase activity of influenza virus A. Contrary to an earlier report, 5-(phosphonomethyl)-1H-tetrazole was not an efficient inhibitor of the replication of HSV-1 and HSV-2 in tissue culture. Analogues of 5-(phosphonomethyl)-1H-tetrazole were also devoid of significant antiviral activity. Only 5-(phosphonomethyl)-1H-tetrazole and 5-(thiophosphonomethyl)-1H-tetrazole inhibited the influenza virus transcriptase, and both were more effective as inhibitors than phosphonoacetic acid under the same conditions. The DNA polymerases induced by HSV-1 and HSV-2 were inhibited slightly by 5-(phosphonomethyl)-1H-tetrazole and to a lesser extent by its N-ethyl analogue and 3-(phosphonomethyl)-1H-1,2,4-triazole. None of these compounds were as effective as phosphonoacetic acid. 5-(Thiophosphonomethyl)-1H-tetrazole was a better inhibitor of the DNA polymerase induced by HSV-1 than 5-(phosphonomethyl)-1H-tetrazole.

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“…When studied using a high‐pressure CI/NH 3 source, the loss of the alkene chain from TBP15 or other phosphates can be rationalised by a single H‐transfer within the MH + ion. Under these conditions, poor intensities of fragment ions are observed because of the low energy deposited on the MH + ion.…”

mentioning

confidence: 99%

Study of mass spectrometric fragmentations of tributyl phosphate via collision‐induced dissociation

Lesage

Virelizier

Tabet

et al. 2001

Rapid Comm Mass Spectrometry

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Tributyl phosphate (TBP) fragmentation mechanisms were studied by mass spectrometry (MS) and tandem mass spectrometry (MS/MS), using electron impact (EI) or chemical (CI) ionisation of the parent compound and its deuterated analogues. The study of this simple compound is essential for the analysis of complex post-radiolysis mixtures and the identification of particular effects arising from the radiolysis or acid hydrolysis of TBP during nuclear fuel reprocessing. Energy-resolved mass spectrometry (ERMS) and isotopic labelling helped to establish the fragment ion connectivities by distinct identification of the competitive and consecutive mechanisms. An ion-dipole intermediate hypothesis, proposed previously in the case of alkyl phosphates and phosphonates in order to explain the mobility of hydrogen atoms from the alkyl chains, is rejected on the basis of the identification of competitive mechanisms in the TBP fragmentation pathways. Copyright The detailed knowledge of these mechanisms can enable the design of new improved solvent systems, as well as improvements in the reprocessing procedures from the study of these compounds unwanted even at trace levels. In this study, we report an investigation by tandem mass spectrometry (MS/MS) of protonated or deuterated tributyl phosphate and its derivatives, by comparing collisioninduced decomposition (CID) of specifically labelled compounds. In a following paper, we will report CID of protonated (or deuterated) TBP dimers formed by radiolytic degradation, which are important because these compounds are potential complexing agents of plutonium. 6 In a previous paper, 7 the structural identification of isomeric TBP dimers was emphasised as a necessary step to understood their behaviour. All of these results, concerning structural identification of TBP dimers and CID of protonated TBP, allow better investigation of minor functionalised degradation product structures generated by radiolysis, as reported in a previous paper. 8The mass spectrum of TBP obtained under EI conditions includes fragment ions involving consecutive losses of butene together with formation of alkyl carbocations. 14 When studied using a high-pressure CI/NH 3 source, the loss of the alkene chain from TBP 15 or other phosphates can be rationalised by a single H-transfer within the MH ion.Under these conditions, poor intensities of fragment ions are observed because of the low energy deposited on the MH ion. However, the high abundance of MH ions easily allows CID studies of these ions. Leroy has studied the CID fragmentation of protonated phosphonates prepared under ammonia chemical ionisation conditions. 16 These results enabled establishment of the proton affinity scale for some phosphonates using Cooks'

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Ammonia chemical ionization mass spectra of esters and amides of oxyacids of phosphorus

Cited by 26 publications

References 5 publications

Selective determination of organophosphate flame retardants and plasticizers in indoor air by gas chromatography, positive‐ion chemical ionization and collision‐induced dissociation mass spectrometry

Selective determination of organophosphate flame retardants and plasticizers in indoor air by gas chromatography, positive‐ion chemical ionization and collision‐induced dissociation mass spectrometry

The antiviral activity of tetrazole phosphonic acids and their analogues

Study of mass spectrometric fragmentations of tributyl phosphate via collision‐induced dissociation

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