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Nitrogen matters: the difference between PANH and PAH formation.

Jordy Bouwman1, Andras Bodi, Patrick Hemberger

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Understanding polycyclic aromatic nitrogen heterocycles (PANHs) formation is crucial. The phenyl + acrylonitrile reaction primarily forms open-chain products, not nitrogen-containing rings, challenging existing models for interstellar and atmospheric PANHs.

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Area of Science:

  • Astrochemistry
  • Chemical Kinetics
  • Combustion Chemistry

Background:

  • Polycyclic aromatic nitrogen heterocycles (PANHs) are prevalent in extraterrestrial environments and are terrestrial carcinogens.
  • Reliable models for PANH formation are essential for understanding their abundance and mitigating emissions.

Purpose of the Study:

  • Investigate the phenyl + acrylonitrile reaction mechanism at high temperatures (600–1200 K).
  • Identify radical intermediates and closed-shell products to elucidate PANH formation pathways.
  • Determine the kinetic vs. thermodynamic control of product distribution.

Main Methods:

  • Utilized a hot microreactor for the reaction.
  • Employed photoion mass-selected threshold photoelectron spectroscopy for isomer-selective identification.
  • Performed Franck-Condon simulations and ab initio calculations.
  • Developed a kinetic model to analyze reaction dynamics.

Main Results:

  • Identified C9H8N˙ radical intermediates and C9H7N products.
  • The reaction is kinetically controlled, favoring four open-chain isomers over the thermodynamically stable quinoline.
  • Observed a stark contrast with the phenyl + vinylacetylene reaction, which forms naphthalene.

Conclusions:

  • The stability of the nitrile group inhibits ring formation in the phenyl + acrylonitrile reaction.
  • Nitrile precursors are unlikely to form nitrogen-containing rings through this pathway.
  • Alternative mechanisms are needed to explain nitrogen incorporation into aromatic systems in the interstellar medium and Titan's atmosphere.