Identification of Perinaphthene Radical in Petroleum Product

Stehling, Ferdinand C.; Bartz, K. W.

doi:10.1063/1.1731655

Cited by 32 publications

(5 citation statements)

References 4 publications

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“…The asphaltene molecules contain clusters of condensed aromatic rings ( 33 Examples are perinaphthyl and triangulyl, the structure of the former being shown in Figure 5,A. The possibility of such structures in petroleum asphaltenes seems particularly reasonable in view of the recent identification of perinaphthyl in a petroleum fraction by Stehling and Bartz (27).…”

Section: Discussionmentioning

confidence: 95%

Investigation of the Nature of Free Radicals in Petroleum Asphaltenes and Related Substances by Electron Spin Resonance.

Yen¹,

Erdman²,

Saraceno³

1962

Anal. Chem.

164

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Section: Discussionmentioning

confidence: 95%

Investigation of the Nature of Free Radicals in Petroleum Asphaltenes and Related Substances by Electron Spin Resonance.

Yen¹,

Erdman²,

Saraceno³

1962

Anal. Chem.

164

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“…The phenalenyl radical, P , is an odd-alternant hydrocarbon with a trigonal planar carbon center surrounded by an antiaromatic 12-carbon ring (Figure ) . An alternative way to talk about this system is as a substituted naphthalene derivative, hence its identification in the early literature as the perinaphthyl radical − or acenaphthenyl in Coulson and Streitweiser’s Dictionary . Various studies during the 1950s and early 1960s established the unusual stability of this free radical (Figure ), − and its monoanion and monocation. , …”

Section: Introductionmentioning

confidence: 99%

“…Even before the radical was detected experimentally, ,, it was suggested that the high symmetry of the species may allow significant resonance stabilization, with the radical electron delocalized around the external (twelve carbon) ring. , P is stable in solution over a period of months, , and is believed to be present in petroleum and some of its derivatives. ,, …”

Section: Introductionmentioning

confidence: 99%

Radical Bonding: Structure and Stability of Bis(Phenalenyl) Complexes of Divalent Metals from across the Periodic Table

Craciun

Donald

2009

Inorg. Chem.

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We examine the bonding possibilities of the bis(phenalenyl) MP(2) sandwich complexes of the divalent metals M = Be, Mg, Ca, Sr, Ba, Zn, Cd, and Hg, at the B3LYP level of theory. The outcome is an extraordinarily diverse class of low symmetry bis(phenalenyl)metal complexes in which bonding preferences and binding enthalpies differ dramatically. The lowest energy group 2 metal MP(2) complexes include an intriguing eta(1),eta(3) BeP(2) structure, and bent eta(6),eta(6) systems for M = Ca, Sr, and Ba. The group 12 bis(phenalenyl) complexes are thermodynamically unstable eta(1),eta(1) slip-sandwich structures. To better understand changes in the structural preferences going from the (eta(6),eta(6)) group 2 to the (eta(1),eta(1)) group 12 complexes, we explored the bonding in the bis(phenalenyl) complexes of transition metals with stable +2 oxidations states between Ca and Zn in period 4. The computed binding enthalpies are large and negative for nearly all of the minimum energy bis(phenalenyl) complexes of the group 2 and the transition metals; they are tiny for MgP(2), and are quite positive for the group 12 systems. The structural preferences and stability of the complexes is a subtle negotiation of several influences: the (un)availability of (n - 1)d and np, orbitals for bonding, the cost of the rehybridization at carbon sites in the phenalenyl rings in preparation for bonding to the metals, and the (P---P) interaction between the phenalenyl radicals.

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“…Among these radicals, perinaphthenyl or phenalenyl radicals is possible. The perinaphthenyl radical was identified in a petroleum fraction by ESR spectroscopy . In marine diesel, the results obtained for hyperfine interaction ( hf ) of free radicals and the discussion regarding organic molecule models indicate that perinaphthenyl radicals are probably responsible for the septet–quartet ESR spectrum of this oil by‐product, as well as being essential components that constitute the marine diesel spectrum after heating .…”

Section: Introductionmentioning

confidence: 98%

ESR and calculations on electronic structure of phenalenyl and phenalenyl derivative radicals

Piccinato

Costa

Ota

et al. 2014

Magnetic Reson in Chemistry

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Calculations on electronic structure of the perinaphthenyl radical and phenalenyl derivative radicals responsible for the composition of the ESR spectrum of marine diesel under heating were performed to obtain support for the experimental ESR results. The parameters calculated were the hyperfine coupling constants (A), which were then used for comparison with the experimental data. The energy-minimized structures were obtained using the density functional theory method. In all cases, the symmetry system was taken into account in theoretical calculations. The differences between experimental and theoretical values were below 7% for nearest hydrogens in molecules, named hyperfine coupling constant A (first neighbors) and 18% for farthest hydrogens atoms named hyperfine coupling constants A' (second neighbors), for all structures analyzed.

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Identification of Perinaphthene Radical in Petroleum Product

Cited by 32 publications

References 4 publications

Investigation of the Nature of Free Radicals in Petroleum Asphaltenes and Related Substances by Electron Spin Resonance.

Investigation of the Nature of Free Radicals in Petroleum Asphaltenes and Related Substances by Electron Spin Resonance.

Radical Bonding: Structure and Stability of Bis(Phenalenyl) Complexes of Divalent Metals from across the Periodic Table

ESR and calculations on electronic structure of phenalenyl and phenalenyl derivative radicals

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