How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C10H7) to benzindenes (C13H10 ) as a case study

Zhao, Long; Prendergast, Matthew; Kaiser, Ralf I.; Xu, Bo; Ablikim, Utuq; Lu, Wenchao; Ahmed, Musahid; Oleinikov, Artem D.; Azyazov, Valeriy N.; Howlader, A. Hasan; Wnuk, Stanislaw F.; Mebel, Alexander M.

doi:10.1039/c9cp02930c

Title: How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C₁₀H₇) to benzindenes (C₁₃H₁₀ ) as a case study

Abstract

The three-ring polycyclic aromatic hydrocarbons (PAHs) 3H-benz[e]indene (C₁₃H₁₀) and 1H-benz[f]indene (C₁₃H₁₀) along with their naphthalene-based isomers 2-(prop-2-yn-1-yl)naphthalene (C₁₃H₁₀), 2-(prop-1-yn-1-yl)naphthalene (C₁₃H₁₀), and 2-(propa-1,2-dien-1-yl)naphthalene (C₁₃H₁₀) were formed through a “directed synthesis” via a high temperature chemical micro reactor under combustion-like conditions (1300 ± 35 K) through the reactions of the 2-naphthyl isomer (C₁₀H₇˙) with allene (C₃H₄) and methylacetylene (C₃H₄). The isomer distributions were probed utilizing tunable vacuum ultraviolet radiation from the Advanced Light Source (ALS) by recording the photoionization efficiency curves at mass-to-charge of m/z = 166 (C₁₃H₁₀) and 167 (¹³CC₁₂H₁₀) of the products in a supersonic molecular beam. Complemented by electronic structure calculations, our study reveals critical mass growth processes via annulation of a five-membered ring from the reaction between aryl radicals and distinct C₃H₄ isomers at elevated temperatures as present in combustion processes and in circumstellar envelopes of carbon stars. The underlying reaction mechanisms proceed through the initial addition of the 2-naphthyl radical with its radical center to the π-electron density of the allene and methylacetylene reactants via entrance barriers between 8 and 14 kJ mol^-1, followed by isomerization (hydrogen shifts, ring closure), and termination via atomic hydrogen losses accompanied by aromatization. The reaction mechanisms reflect the formation of indenemore »« less

Authors:

^[1]; Prendergast, Matthew ^[1];

^[1]; Xu, Bo ^[2]; Ablikim, Utuq ^[2];

^[2];

^[3];

^[4];

^[5]

Univ. of Hawaii, Manoa, HI (United States)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Samara National Research Univ. (Russia)
Florida International Univ., Miami, FL (United States)
Florida International Univ., Miami, FL (United States); Samara National Research Univ. (Russia)

Publication Date:: Thu Jul 11 00:00:00 EDT 2019

Research Org.:: Florida International Univ. (FIU), Miami, FL (United States); Univ. of Hawaii, Honolulu, HI (United States); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

OSTI Identifier:: 1603183

Alternate Identifier(s):: OSTI ID: 1543171; OSTI ID: 1608273

Grant/Contract Number:: FG02-04ER15570; FG02-03ER15411; AC02-05CH11231; 14.Y26.31.0020

Resource Type:: Accepted Manuscript

Journal Name:: Physical Chemistry Chemical Physics. PCCP

Additional Journal Information:: Journal Volume: 21; Journal Issue: 30; Journal ID: ISSN 1463-9076

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

Subject:: 74 ATOMIC AND MOLECULAR PHYSICS; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Zhao, Long, Prendergast, Matthew, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Lu, Wenchao, Ahmed, Musahid, Oleinikov, Artem D., Azyazov, Valeriy N., Howlader, A. Hasan, Wnuk, Stanislaw F., and Mebel, Alexander M. How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C10H7) to benzindenes (C13H10 ) as a case study.  United States: N. p., 2019. 
Web.  doi:10.1039/c9cp02930c.

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                    Zhao, Long, Prendergast, Matthew, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Lu, Wenchao, Ahmed, Musahid, Oleinikov, Artem D., Azyazov, Valeriy N., Howlader, A. Hasan, Wnuk, Stanislaw F., & Mebel, Alexander M. How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C10H7) to benzindenes (C13H10 ) as a case study.  United States.  https://doi.org/10.1039/c9cp02930c

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                    Zhao, Long, Prendergast, Matthew, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Lu, Wenchao, Ahmed, Musahid, Oleinikov, Artem D., Azyazov, Valeriy N., Howlader, A. Hasan, Wnuk, Stanislaw F., and Mebel, Alexander M. Thu .  
"How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C10H7) to benzindenes (C13H10 ) as a case study".  United States.  https://doi.org/10.1039/c9cp02930c.  https://www.osti.gov/servlets/purl/1603183.

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@article{osti_1603183,

  title        = {How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C10H7) to benzindenes (C13H10 ) as a case study},

  author       = {Zhao, Long and Prendergast, Matthew and Kaiser, Ralf I. and Xu, Bo and Ablikim, Utuq and Lu, Wenchao and Ahmed, Musahid and Oleinikov, Artem D. and Azyazov, Valeriy N. and Howlader, A. Hasan and Wnuk, Stanislaw F. and Mebel, Alexander M.},

  abstractNote = {The three-ring polycyclic aromatic hydrocarbons (PAHs) 3H-benz[e]indene (C13H10) and 1H-benz[f]indene (C13H10) along with their naphthalene-based isomers 2-(prop-2-yn-1-yl)naphthalene (C13H10), 2-(prop-1-yn-1-yl)naphthalene (C13H10), and 2-(propa-1,2-dien-1-yl)naphthalene (C13H10) were formed through a “directed synthesis” via a high temperature chemical micro reactor under combustion-like conditions (1300 ± 35 K) through the reactions of the 2-naphthyl isomer (C10H7˙) with allene (C3H4) and methylacetylene (C3H4). The isomer distributions were probed utilizing tunable vacuum ultraviolet radiation from the Advanced Light Source (ALS) by recording the photoionization efficiency curves at mass-to-charge of m/z = 166 (C13H10) and 167 (13CC12H10) of the products in a supersonic molecular beam. Complemented by electronic structure calculations, our study reveals critical mass growth processes via annulation of a five-membered ring from the reaction between aryl radicals and distinct C3H4 isomers at elevated temperatures as present in combustion processes and in circumstellar envelopes of carbon stars. The underlying reaction mechanisms proceed through the initial addition of the 2-naphthyl radical with its radical center to the π-electron density of the allene and methylacetylene reactants via entrance barriers between 8 and 14 kJ mol-1, followed by isomerization (hydrogen shifts, ring closure), and termination via atomic hydrogen losses accompanied by aromatization. The reaction mechanisms reflect the formation of indene – the prototype PAH carrying a single five- and a single six-membered ring – synthesized through the reaction of the phenyl radical (C6H5˙) with allene and methylacetylene. In conclusion, this leads us to predict that aryl radicals – upon reaction with allene/methylacetylene – may undergo molecular mass growth processes via ring annulation and de facto addition of a five-membered ring to form molecular building blocks essential to transit planar PAHs out of the plane.},

  doi          = {10.1039/c9cp02930c},

  journal      = {Physical Chemistry Chemical Physics. PCCP},

  number       = 30,

  volume       = 21,

  place        = {United States},

  year         = {Thu Jul 11 00:00:00 EDT 2019},

  month        = {Thu Jul 11 00:00:00 EDT 2019}

}

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Scheme 1: Prototype polycyclic aromatic hydrocarbon naphthalene together with (di)methyl substituted counterparts formed in the reactions of phenyl-type radicals (phenyl, tolyl).

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Zhang, Taichang; Zhang, Lidong; Hong, Xin
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Baboul, Anwar G.; Curtiss, Larry A.; Redfern, Paul C.
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Li, Yuyang; Zhang, Lidong; Tian, Zhenyu
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Bittner, J. D.; Howard, J. B.
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ChemPhysChem, Vol. 20, Issue 6
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Unexpected Chemistry from the Reaction of Naphthyl and Acetylene at Combustion-Like Temperatures
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Parker, Dorian S. N.; Kaiser, Ralf. I.; Bandyopadhyay, Biswajit
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Works referencing / citing this record:

Influence of early stages of triglyceride pyrolysis on the formation of PAHs as coke precursors
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Kozliak, Evguenii; Sulkes, Mark; Alhroub, Ibrahim
Physical Chemistry Chemical Physics, Vol. 21, Issue 36
DOI: 10.1039/c9cp02025j

Figures / Tables found in this record:

Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.

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Gas phase formation of cyclopentanaphthalene (benzindene) isomers via reactions of 5- and 6-indenyl radicals with vinylacetylene

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Title: How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C10H7) to benzindenes (C13H10 ) as a case study

Abstract

Citation Formats

Figures / Tables:

Beyond the obvious: Environmental health implications of polar polycyclic aromatic hydrocarbons journal, February 2019

Aromatic and Polycyclic Aromatic Hydrocarbon Formation in a Laminar Premixed n-Butane Flame journal, July 1998

Pyrene synthesis in circumstellar envelopes and its role in the formation of 2D nanostructures journal, March 2018

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An experimental study of the premixed benzene/oxygen/argon flame with tunable synchrotron photoionization journal, January 2007

Dynamical Resonances in the Fluorine Atom Reaction with the Hydrogen Molecule journal, August 2008

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Soot formation in binary hydrocarbon mixtures journal, July 1988

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Reformulation and Solution of the Master Equation for Multiple-Well Chemical Reactions journal, May 2013

Reaction of Phenyl Radicals with Propyne journal, February 2002

Pressure-dependent rate constants for PAH growth: formation of indene and its conversion to naphthalene journal, January 2016

Indene Formation under Single-Collision Conditions from the Reaction of Phenyl Radicals with Allene and Methylacetylene-A Crossed Molecular Beam and Ab Initio Study journal, September 2011

Fuel-rich flame chemistry in low-pressure cyclopentene flames journal, January 2000

Temperature- and pressure-dependent rate coefficients for the HACA pathways from benzene to naphthalene journal, January 2017

Pahs and Astrobiology journal, January 2011

Gaussian-3 theory using coupled cluster energies journal, November 1999

The effects of equivalence ratio on the formation of polycyclic aromatic hydrocarbons and soot in premixed ethane flames journal, June 2000

The Formation of Nitriles in Hydrocarbon-Rich Atmospheres of Planets and Their Satellites: Laboratory Investigations by the Crossed Molecular Beam Technique journal, September 2001

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An experimental and theoretical study of toluene pyrolysis with tunable synchrotron VUV photoionization and molecular-beam mass spectrometry journal, November 2009

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Gaussian-3 theory using density functional geometries and zero-point energies journal, April 1999

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Title: How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C₁₀H₇) to benzindenes (C₁₃H₁₀ ) as a case study

Beyond the obvious: Environmental health implications of polar polycyclic aromatic hydrocarbons
journal, February 2019

Aromatic and Polycyclic Aromatic Hydrocarbon Formation in a Laminar Premixed n-Butane Flame
journal, July 1998

Pyrene synthesis in circumstellar envelopes and its role in the formation of 2D nanostructures
journal, March 2018

Analysis of pyrolysis products from light hydrocarbons and kinetic modeling for growth of polycyclic aromatic hydrocarbons with detailed chemistry
journal, September 2009

The Reaction of Phenyl Radical with Molecular Oxygen: A G2M Study of the Potential Energy Surface
journal, July 2005

A VUV Photoionization Study of the Formation of the Indene Molecule and Its Isomers
journal, June 2011

The molecular universe
journal, July 2013

Low-temperature formation of polycyclic aromatic hydrocarbons in Titan’s atmosphere
journal, October 2018

Thermodynamic properties of the species resulting from the phenyl radical with O ₂ reaction system
journal, September 2008

Formation of 5- and 6-methyl-1H-indene (C ₁₀ H ₁₀ ) via the reactions of the para-tolyl radical (C ₆ H ₄ CH ₃ ) with allene (H ₂ CCCH ₂ ) and methylacetylene (HCCCH ₃ ) under single collision conditions
journal, January 2015

C ROSSED -B EAM S TUDIES OF N EUTRAL R EACTIONS : State-Specific Differential Cross Sections
journal, October 2001

Investigation of the rich premixed laminar acetylene/oxygen/argon flame: Comprehensive flame structure and special concerns of polyynes
journal, January 2009

The effects of equivalence ratio on the formation of polycyclic aromatic hydrocarbons and soot in premixed methane flames
journal, January 1998

Selective Formation of Indene through the Reaction of Benzyl Radicals with Acetylene
journal, April 2015

Detection of Benz[ f ]indene among the Pyrolysis Products of Coal and Anthracene
journal, September 1999

Environmental Concerns and Toxicogenetic Endpoints of Priority Substances (PSs) and Contaminants of Emerging Concerns (CECs): A Comprehensive Review
journal, March 2018

Infrared Spectroscopy of Interstellar Dust
journal, January 2009

Children environmental exposure to particulate matter and polycyclic aromatic hydrocarbons and biomonitoring in school environments: A review on indoor and outdoor exposure levels, major sources and health impacts
journal, March 2019

Photochemical and Discharge-Driven Pathways to Aromatic Products from 1,3-Butadiene
journal, November 2007

Experimental Investigation on the Formation of Carbon-Bearing Molecules in the Interstellar Medium via Neutral−Neutral Reactions
journal, May 2002

Improved sooting tendency measurements for aromatic hydrocarbons and their implications for naphthalene formation pathways
journal, March 2007

A VUV Photoionization Study of the Combustion-Relevant Reaction of the Phenyl Radical (C ₆ H ₅ ) with Propylene (C ₃ H ₆ ) in a High Temperature Chemical Reactor
journal, March 2012

Investigation on fuel-rich premixed flames of monocyclic aromatic hydrocarbons: Part I. Intermediate identification and mass spectrometric analysis
journal, January 2010

Low temperature formation of naphthalene and its role in the synthesis of PAHs (Polycyclic Aromatic Hydrocarbons) in the interstellar medium
journal, December 2011

Ab Initio G3-type/Statistical Theory Study of the Formation of Indene in Combustion Flames. I. Pathways Involving Benzene and Phenyl Radical ^†
journal, May 2007

An Ab Initio G3-Type/Statistical Theory Study of the Formation of Indene in Combustion Flames. II. The Pathways Originating from Reactions of Cyclic C ₅ SpeciesCyclopentadiene and Cyclopentadienyl Radicals
journal, January 2008

A VUV photoionization study of the multichannel reaction of phenyl radicals with 1,3-butadiene under combustion relevant conditions
journal, January 2013

VUV Photoionization Study of the Formation of the Simplest Polycyclic Aromatic Hydrocarbon: Naphthalene (C ₁₀ H ₈ )
journal, May 2018

Experimental study of PAH formation in laminar counterflow CH4N2/O2N2 and C3H8N2/O2N2 nonpremixed flames
journal, July 2005

The formation of aromatic hydrocarbons at high temperatures. XXVI. Pyrolysis of [1-14C]styrene
journal, January 1966

Pyrolytic Hydrocarbon Growth from Cyclopentadiene
journal, December 2010

Formation of polycyclic aromatic hydrocarbons in circumstellar envelopes
journal, June 1989

Effect of fuel structure on pathways to soot
journal, January 1988

Treatment technologies for PAH-contaminated sites: a critical review
journal, August 2018

Phenoxy Radical (C ₆ H ₅ O) Formation under Single Collision Conditions from Reaction of the Phenyl Radical (C ₆ H ₅ , X ² A ₁ ) with Molecular Oxygen (O ₂ , X ³ Σ _g ^– ): The Final Chapter?
journal, October 2011

Calculations of Rate Coefficients for the Chemically Activated Reactions of Acetylene with Vinylic and Aromatic Radicals
journal, November 1994

Photoinduced Mechanism of Formation and Growth of Polycyclic Aromatic Hydrocarbons in Low-Temperature Environments via Successive Ethynyl Radical Additions
journal, October 2008

Formation of polycyclic aromatic hydrocarbons in an atmospheric pressure ethylene diffusion flame
journal, August 1999

Soot formation in high pressure laminar diffusion flames
journal, December 2012

Formation of small PAHs in laminar premixed low-pressure propene and cyclopentene flames: Experiment and modeling
journal, January 2008

Benzoxyl Radical Decomposition Kinetics: Formation of Benzaldehyde + H, Phenyl + CH ₂ O, and Benzene + HCO
journal, June 2009

Pyrolysis of furan in a microreactor
journal, September 2013

Combustion chemistry probed by synchrotron VUV photoionization mass spectrometry
journal, January 2013

Reaction Dynamics of Phenyl Radicals in Extreme Environments: A Crossed Molecular Beam Study
journal, February 2009

Formation mechanism of polycyclic aromatic hydrocarbons and fullerenes in premixed benzene flames
journal, October 1999

Formation of the diphenyl molecule in the crossed beam reaction of phenyl radicals with benzene
journal, February 2008

Detailed Kinetic Study of the Growth of Small Polycyclic Aromatic Hydrocarbons. 1. 1-Naphthyl + Ethyne ^†
journal, March 2001

PAH emissions from high-temperature oxidation of vaporized anthracene
journal, January 2007

Investigation on the pyrolysis and oxidation of toluene over a wide range conditions. I. Flow reactor pyrolysis and jet stirred reactor oxidation
journal, January 2015

An experimental study of the premixed benzene/oxygen/argon flame with tunable synchrotron photoionization
journal, January 2007

Dynamical Resonances in the Fluorine Atom Reaction with the Hydrogen Molecule
journal, August 2008

Elementary reactions of the phenyl radical, C$_\mathsf{6}$H$_\mathsf{5}$, with C$_\mathsf{3}$H$_\mathsf{4}$ isomers, and of benzene, C$_\mathsf{6}$H$_\mathsf{6}$, with atomic carbon in extraterrestrial environments
journal, August 2003

Reactions of chemically activated C9H9 species.
journal, April 2002

Detailed modeling of soot particle nucleation and growth
journal, January 1991

Soot formation in binary hydrocarbon mixtures
journal, July 1988

Gas‐Phase Synthesis of Triphenylene (C ₁₈ H ₁₂ )
journal, March 2019

Reformulation and Solution of the Master Equation for Multiple-Well Chemical Reactions
journal, May 2013

Reaction of Phenyl Radicals with Propyne
journal, February 2002

Pressure-dependent rate constants for PAH growth: formation of indene and its conversion to naphthalene
journal, January 2016

Indene Formation under Single-Collision Conditions from the Reaction of Phenyl Radicals with Allene and Methylacetylene-A Crossed Molecular Beam and Ab Initio Study
journal, September 2011

Fuel-rich flame chemistry in low-pressure cyclopentene flames
journal, January 2000

Temperature- and pressure-dependent rate coefficients for the HACA pathways from benzene to naphthalene
journal, January 2017

Pahs and Astrobiology
journal, January 2011

Gaussian-3 theory using coupled cluster energies
journal, November 1999

The effects of equivalence ratio on the formation of polycyclic aromatic hydrocarbons and soot in premixed ethane flames
journal, June 2000

The Formation of Nitriles in Hydrocarbon-Rich Atmospheres of Planets and Their Satellites: Laboratory Investigations by the Crossed Molecular Beam Technique
journal, September 2001

Toward the Oxidation of the Phenyl Radical and Prevention of PAH Formation in Combustion Systems
journal, November 2014

Dynamics of Chlorine Atom Reactions with Hydrocarbons: Insights from Imaging the Radical Product in Crossed Beams
journal, August 2014

Formation Mechanisms of Naphthalene and Indene: From the Interstellar Medium to Combustion Flames
journal, January 2017

Interstellar Polycyclic Aromatic Hydrocarbon Molecules
journal, September 2008

Unexpected Chemistry from the Reaction of Naphthyl and Acetylene at Combustion-Like Temperatures
journal, March 2015

High Pressure Pyrolysis of Toluene. 2. Modeling Benzyl Decomposition and Formation of Soot Precursors
journal, August 2006

An experimental and theoretical study of toluene pyrolysis with tunable synchrotron VUV photoionization and molecular-beam mass spectrometry
journal, November 2009

Gaussian-3 (G3) theory for molecules containing first and second-row atoms
journal, November 1998

Gaussian-3 theory using density functional geometries and zero-point energies
journal, April 1999

Experimental Study of a Fuel-Rich Premixed Toluene Flame at Low Pressure
journal, March 2009

Composition profiles and reaction mechanisms in a near-sooting premixed benzene/oxygen/argon flame
journal, January 1981

Water acting as a catalyst for electron-driven molecular break-up of tetrahydrofuran
journal, May 2020

Gas‐Phase Synthesis of Triphenylene (C ₁₈ H ₁₂ )
journal, February 2019