Synthesis of 1‐ and 3‐Nitrobenzo[<i>a</i>]pyrene

Dyker, Gerald; Kadzimirsz, Daniel; Thöne, Andreas

doi:10.1002/ejoc.200300216

Cited by 8 publications

(5 citation statements)

References 21 publications

(10 reference statements)

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“…The standards used for PAH analysis were the same as described in a preceding publication [36]. 1-nitrobenzo[a]pyrene (1-NBaP) and 3-nitrobenzo[a]pyrene (3-NBaP) (>98%) were synthesized by Dyker et al [37]. Calibration standard solutions were prepared with cyclohexane and diluted to the required concentrations before use.…”

Section: Methodsmentioning

confidence: 99%

Analysis of nitrated polycyclic aromatic hydrocarbons by liquid chromatography with fluorescence and mass spectrometry detection: air particulate matter, soot, and reaction product studies

Schauer

Pöschl

2004

Analytical and Bioanalytical Chemistry

100

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Polycyclic aromatic hydrocarbons (PAH) and their nitrated derivatives (nitro-PAH) are environmental pollutants which pose a threat to human health even at low concentration levels. In this study, efficient analytical methods for the analysis of nitro-PAH and PAH (extraction, clean-up, chromatographic separation, and spectrometric detection) have been developed, characterized, and applied to aerosol samples. The separation and quantification of 12 nitro-PAH was carried out by reversed-phase high performance liquid chromatography (HPLC), on-line reduction, and fluorescence detection. The detection limits were in the range of 0.03-0.5 microg L(-1) (6-100 pg in the investigated sample aliquots), and the recovery rates from soot samples were 70-90%. Nitro-PAH and PAH concentrations have been determined for different types of soot and for urban, rural, and alpine fine air particulate matter (PM2.5). For the first time, trace amounts of nitro-PAH have been detected in a high-alpine clean air environment. The on-line reduction and fluorescence technique has been complemented by atmospheric pressure chemical ionization time-of-flight mass spectrometry (APCI-TOF-MS). The MS detection allowed the analysis of partially nitrated and oxygenated PAH in laboratory studies of the heterogeneous reaction of PAH on soot and glass fiber substrates with gaseous nitrogen oxides and ozone. It led to the tentative identification of a previously unknown nitrated derivative of the particularly toxic PAH benzo[ a]pyrene (BaP-nitroquinone), and provides the first experimental evidence that PAH-nitroquinones can be formed by reaction of PAH with atmospheric photooxidants.

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Section: Methodsmentioning

confidence: 99%

Analysis of nitrated polycyclic aromatic hydrocarbons by liquid chromatography with fluorescence and mass spectrometry detection: air particulate matter, soot, and reaction product studies

Schauer

Pöschl

2004

Analytical and Bioanalytical Chemistry

100

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“…Dyker et al . reported the synthesis of 1- and 3-nitrobenzo[ a ]pyrene (1-NBaP, 3-NBaP) and, as part of their analytical characterization, reported the frequencies of a few of the major infrared bands.…”

Section: Introductionmentioning

confidence: 99%

“…Dyker et al. 25 reported the synthesis of 1-and 3-nitrobenzo[a]pyrene (1-NBaP, 3-NBaP) and, as part of their analytical characterization, reported the frequencies of a few of the major infrared bands. Because comprehensive experimental and theoretical studies of the important monosubstituted NBaPs are lacking, this study was undertaken with the following objectives:…”

Section: Introductionmentioning

confidence: 99%

Structure and Vibrational Spectra of Mononitrated Benzo[a]pyrenes

2005

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The molecules benzo[a]pyrene (BaP) and 1-, 3-, and 6-nitrobenzo[a]pyrene (1-NBaP, 3-NBaP, 6-NBaP) are currently of significant interest due to their presence in respirable combustion exhaust particulates and their mutagenic and carcinogenic properties. Structure-function correlations as well as spectroscopic signatures for trace analysis are necessary for these benzo[a]pyrene derivatives. In this paper, detailed infrared and Raman spectroscopic data of BaP and its three mononitrated isomers are provided for the first time. By utilizing density functional theory (DFT, B3LYP method with 6-311+G basis set), the molecular geometries and the vibrational spectra are calculated. Good agreement is noted between the calculated and experimental geometry for BaP, and predictions of the vibrational data for all compounds are within approximately 5 cm-1 of the experimental data. Normal mode assignments are proposed with particular emphasis on the nitro group vibrations. The geometrical distortions of the BaP structure upon nitro group substitution and correlations between structural parameters and vibrational data as well as structure-function relationships related to the mutagenicity of this important class of polycyclic aromatic hydrocarbons are discussed.

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“…The 1 H NMR spectra of BaP, 1-, 3- and 6-NBaP have been assigned previously in CDCl 3 in acetone-d 6 and DMSO [3,[8], [9], [10]]. Of relevance in this article are the 13 C NMR peaks.…”

Section: Experimental Design Materials and Methodsmentioning

confidence: 82%

“…While one study reports 13 C NMR assignments of 1-, and 3-NBaP in DMSO [9] none is available for 6-NBaP. The current study assigned 13 C chemical shifts of three mononitrated benzo( a )pyrenes in CDCl 3 via heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple-bond connectivity (HMBC) methods (ref # [11]).…”

Section: Experimental Design Materials and Methodsmentioning

confidence: 99%

Data on GC/MS elution profile, 1H and 13C NMR spectra of 1-, 3-, and 6-Nitrobenzo[a]pyrenes

Onchoke

2020

Data in Brief

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The data presented in this article is related to the research article entitled, “13C NMR Chemical Shift Assignments of Nitrated Benzo[a]pyrenes based on Two-dimensional Techniques and DFT/GIAO Calculations”, Kefa K. Onchoke, J. Chem. Sci. (2020) [1]. The NMR spectral profiles of nitrated benzo[a]pyrenes is presented. Further, the article describes elution profiles of 1-, 3- and 6-NBaP, the acquisition of 1H and 13C NMR data and the J-Coupling constants (which are useful for the assignment of peaks via 2D HMQC and HMBC techniques). The data presented is useful for developing structure-activity relationships for other nitrated polycyclic aromatic hydrocarbons (NPAHs).

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Synthesis of 1‐ and 3‐Nitrobenzo[a]pyrene

Abstract: The synthesis of the important carcinogens 1-nitrobenzo[a]-pyrene and 3-nitrobenzo[a]pyrene was achieved in four steps starting from the parent compound. A hexyl ester functionality was introduced as a removable blocking group, controlling the regioselectivity of the synthesis.

Cited by 8 publications

References 21 publications

Analysis of nitrated polycyclic aromatic hydrocarbons by liquid chromatography with fluorescence and mass spectrometry detection: air particulate matter, soot, and reaction product studies

Analysis of nitrated polycyclic aromatic hydrocarbons by liquid chromatography with fluorescence and mass spectrometry detection: air particulate matter, soot, and reaction product studies

Structure and Vibrational Spectra of Mononitrated Benzo[a]pyrenes

Data on GC/MS elution profile, 1H and 13C NMR spectra of 1-, 3-, and 6-Nitrobenzo[a]pyrenes

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