Formation of bicyclic polycyclic aromatic hydrocarbons (PAHs) from the reaction of a phenyl radical with <i>cis</i>-3-penten-1-yne

Wei, Mingrui; Zhang, Tingting; Chen, Xianfeng; Yan, Fuwu; Guo, Guanlun; Zhang, Dongju

doi:10.1039/c8ra01449c

Cited by 4 publications

(2 citation statements)

References 55 publications

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“…whose structure contains five-membered carbon rings, which have already been proposed in the literature to be important intermediates on the formation of NSPs 11,12,[55][56][57][58] . CP-PAHs often share the same molecular formula as six-membered ring PAHs, and are thus impossible to distinguish with common mass spectrometry setups.…”

Section: Introductionmentioning

confidence: 96%

Selective identification of cyclopentaring-fused PAHs and side-substituted PAHs in a low pressure premixed sooting flame by photoelectron photoion coincidence spectroscopy

Mercier

Faccinetto

Batut

et al. 2020

Phys. Chem. Chem. Phys.

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Section: Introductionmentioning

confidence: 96%

Selective identification of cyclopentaring-fused PAHs and side-substituted PAHs in a low pressure premixed sooting flame by photoelectron photoion coincidence spectroscopy

Mercier

Faccinetto

Batut

et al. 2020

Phys. Chem. Chem. Phys.

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“…For example, isoprene (C 5 H 8 ) and the methyl-substituted 1,3butadiene can form phenyl radical with very low activation energy [24]. Earlier, in 2001, Zhang et al had proposed the formation of bicyclic PAHs from phenyl radicals reacting with cis-3-penten-1-yne [25]. Later, formation of naphthalene had been identified as a result of bimolecular recombination of paratolyl and phenyl radicals using crossed molecular beam experiments and higher order PAHs like anthracene and phenanthrene had been prepared in low temperature environments [26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Theoretical Investigation on C11H8 Bicyclic Carbene and Allene Isomers

et al. 2022

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Recent studies postulate that the presence of polycyclic aromatic hydrocarbons (PAHs) in the interstellar medium (ISM) could have been formed through resonance-stabilized arylcarbene intermediates. However, identifying most of these reactive intermediates is very challenging experimentally due to their metastability and other experimental constrains. Thus, computational studies that cover the thermodynamic versus kinetic stability of various possible structures would be beneficial for successfully identifying new molecules either in the laboratory and/or in the ISM. In this paper, more than four hundred C11H8 carbene isomers have been theoretically investigated employing density functional theory (DFT). Hybrid density functionals B3LYP and ωB97XD with 6-311 + G (d,p) basis set have been used for singlet electronic states, whereas, triplet spin states were optimized at the same level using an unrestricted Hartree-Fock wavefunction. Although the skeletal structures of C11H8 can be categorized into monocyclic, bicyclic, tricyclic, tetracyclic and acyclic isomers, bicyclic carbenes have shown better stability due to the presence of resonance stabilized azulenyl/naphthyl rings. In this category, some isomers (1-, 2-, 5- and 6-azulenylcarbenes and 1- and 2-naphthylcarbenes) have also been detected recently in the laboratory and simple aromatic carbenes such as cyclopropenylidene and its homologues are detected in the ISM. Thus, we have systematically investigated the energetic and spectroscopic properties of resonance stabilized 5-, 6-, 7- and 8-membered ring containing bicyclic isomers of C11H8 and the fingerprint regions of the infrared spectrum for each class of these bicyclic compounds.

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The formation of PBDFs from the ortho-disubstituted phenol precursors: A comprehensive theoretical study on the PBDD/Fs formation from 2,4,6-tribromophenol

Chang

Pan

Liu

et al. 2020

Science of The Total Environment

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Formation of bicyclic polycyclic aromatic hydrocarbons (PAHs) from the reaction of a phenyl radical with cis-3-penten-1-yne

Abstract: The formation of PAHs within 4-, 5-, 6- and 7-membered rings on the C6H5 + C5H6 potential energy surface.

Cited by 4 publications

References 55 publications

Selective identification of cyclopentaring-fused PAHs and side-substituted PAHs in a low pressure premixed sooting flame by photoelectron photoion coincidence spectroscopy

Selective identification of cyclopentaring-fused PAHs and side-substituted PAHs in a low pressure premixed sooting flame by photoelectron photoion coincidence spectroscopy

Theoretical Investigation on C11H8 Bicyclic Carbene and Allene Isomers

The formation of PBDFs from the ortho-disubstituted phenol precursors: A comprehensive theoretical study on the PBDD/Fs formation from 2,4,6-tribromophenol

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