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On the formation of nitrogen-substituted polycyclic aromatic hydrocarbons (NPAHs) in circumstellar and interstellar environments

Journal Article · · Chemical Society Reviews
DOI:https://doi.org/10.1039/c6cs00714g· OSTI ID:1602959
 [1];  [2]
  1. Univ. of Hawaii at Manoa, Honolulu, HI (United States); University of Hawaii at Manoa
  2. Univ. of Hawaii at Manoa, Honolulu, HI (United States)
+ Show Author Affiliations

The chemical evolution of extraterrestrial environments leads to the formation of polycyclic aromatic hydrocarbons (PAHs) via gas phase radical mediated aromatization reactions. Here, we review that these de facto barrierless reactions are capable of forming prebiotic molecules such as nitrogen substituted PAHs (NPAHs), which represent the missing link between nitrogen bearing acyclic molecules and prebiotic nucleobases along with vitamins found in meteorites. Crucial routes leading to the incorporation of nitrogen atoms into the aromatic ring have been exposed. Pyridine can be formed from the reaction of abundant vinyl cyanide and its radical or via cyano radicals reacting with 1,3-butadiene. The NPAHs 1,4-dihydro(iso)quinoline and (iso)quinoline can be synthesized through reaction of pyridyl radicals with 1,3-butadiene or sequentially with two acetylene molecules, respectively. The inclusion of nitrogen into an aromatic system and their growth can fill the mechanistic gaps missing leading from acyclic nitrogen-bearing molecules via pyridine to NPAH-type molecules in the interstellar medium.

Research Organization:
Univ. of Hawaii at Manoa, Honolulu, HI (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Grant/Contract Number:
FG02-03ER15411
OSTI ID:
1602959
Alternate ID(s):
OSTI ID: 1535128
Journal Information:
Chemical Society Reviews, Journal Name: Chemical Society Reviews Journal Issue: 2 Vol. 46; ISSN 0306-0012; ISSN CSRVBR
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

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Decomposition of Picolyl Radicals at High Temperature: A Mass Selective Threshold Photoelectron Spectroscopy Study journal November 2019
On the formation and the isomer specific detection of methylacetylene (CH 3 CCH), propene (CH 3 CHCH 2 ), cyclopropane (c-C 3 H 6 ), vinylacetylene (CH 2 CHCCH), and 1,3-butadiene (CH 2 CHCHCH 2 ) from interstellar methane ice analogues journal January 2019
Nitrogen matters: the difference between PANH and PAH formation journal January 2018
Isoquinoline gas-phase absorption spectrum in the vacuum ultraviolet between 3.7 and 10.7 eV. New valence and Rydberg electronic states journal January 2019
On the formation of phosphorous polycyclic aromatics hydrocarbons (PAPHs) in astrophysical environments journal January 2019
Synthesis of functionalized nitrogen-containing polycyclic aromatic hydrocarbons and other prebiotic compounds in impacting glycine solutions journal January 2019
The effect of heteroatoms in carbonaceous surfaces: computational analysis of H chemisorption on to a PANH and Si-doped PAH journal August 2019

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY