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Aromatic Hydrocarbon Anions: Structural Overview01:18

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
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In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
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An improved method for determining dermal exposure to polycyclic aromatic hydrocarbons.

Bo Strandberg1, Anneli Julander2, Mattias Sjöström3

  • 1Division of Occupational and Environmental Medicine, Lund University, Lund, Sweden; Section of Occupational and Environmental Medicine, Institute of Medicine, Sahlgrenska Academy at the University of Gothenburg, Gothenburg, Sweden.

Chemosphere
|February 9, 2018
PubMed
Summary

This study optimized a method to measure polycyclic aromatic hydrocarbons (PAHs) on skin using tape-stripping and dialysis. The new technique accurately detects PAHs, revealing dermal exposure in both workers and controls.

Keywords:
Dermal exposurePAHsSemipermeable membranesTape-strips

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Area of Science:

  • Environmental Health
  • Analytical Chemistry
  • Occupational Medicine

Background:

  • Workers face occupational exposure to polycyclic aromatic hydrocarbons (PAHs), known carcinogens.
  • Dermal exposure is a significant route for PAHs, alongside air sampling.
  • Current methods for analyzing skin-adsorbed PAHs face challenges with co-eluting substances.

Purpose of the Study:

  • To optimize an analytical clean-up procedure for 32 PAHs extracted from tape-strips.
  • To develop a method for assessing dermal PAH exposure using semipermeable membrane dialysis.
  • To validate the optimized method's precision and repeatability.

Main Methods:

  • Extraction of 32 PAHs from tape-strips using organic solvent.
  • Dialysis in organic solvent with semipermeable membranes for clean-up.
  • Analysis of PAHs using gas chromatography/mass spectrometry (GC/MS).

Main Results:

  • The developed method demonstrated acceptable precision and repeatability for 32 PAHs and a certified reference material.
  • PAHs were detected on the skin of both firefighters and control subjects.
  • The optimized procedure successfully assessed dermal exposure to multiple PAHs, including gaseous and particle-bound forms.

Conclusions:

  • The optimized semipermeable membrane dialysis procedure is effective for analyzing PAHs from tape-strip extracts.
  • This method allows for the assessment of dermal PAH exposure in occupational and general populations.
  • Both gaseous and particle-bound PAHs, including alkylated species, can be present on human skin.