Acenaphthene

• Formula: C₁₂H₁₀
• Molecular weight: 154.2078
• IUPAC Standard InChI: InChI=1S/C12H10/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-6H,7-8H2 Copy

  
• IUPAC Standard InChIKey: CWRYPZZKDGJXCA-UHFFFAOYSA-N Copy
• CAS Registry Number: 83-32-9
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Isotopologues:
  • Acenaphthene-d10
• Other names: Acenaphthylene, 1,2-dihydro-; Peri-Ethylenenaphthalene; Naphthyleneethylene; 1,2-Dihydroacenaphthylene; 1,8-Ethylenenaphthalene; Acenaphtene
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
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Gas phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₁₂H₁₀⁺ +  = (C₁₂H₁₀⁺ • )

By formula: C₁₂H₁₀⁺ + C₁₂H₁₀ = (C₁₂H₁₀⁺ • C₁₂H₁₀)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₁₂H₈⁺ +  = (C₁₂H₈⁺ • )

By formula: C₁₂H₈⁺ + C₁₂H₁₀ = (C₁₂H₈⁺ • C₁₂H₁₀)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₁₂H₁₁⁺ +  = (C₁₂H₁₁⁺ • )

By formula: C₁₂H₁₁⁺ + C₁₂H₁₀ = (C₁₂H₁₁⁺ • C₁₂H₁₀)

Free energy of reaction

C₁₂H₉^- +  =

By formula: C₁₂H₉^- + H⁺ = C₁₂H₁₀

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₁₂H₁₀ = (C₆H₇N⁺ • C₁₂H₁₀)

Bond type: Charge transfer bond (positive ion)

2 +  =

By formula: 2H₂ + C₁₂H₁₀ = hexahydroacenaphthylene

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₁₂H₁₀⁺ (ion structure unspecified)

Proton affinity at 298K

Gas basicity at 298K

Ionization energy determinations

De-protonation reactions

C₁₂H₉^- +  =

By formula: C₁₂H₉^- + H⁺ = C₁₂H₁₀

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Roux, Temprado, et al., 2008
Roux, M.V.; Temprado, M.; Chickos, J.S.; Nagano, Y., Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons, J. Phys. Chem. Ref. Data, 2008, 37, 4, 1855-1996. [all data]

Boyd, Christensen, et al., 1965
Boyd, R.H.; Christensen, R.L.; Pua, R., The heats of combustion of acenaphthene, acenaphthylene, and fluoranthene. Strain and delocalization in bridged naphthalenes, J. Am. Chem. Soc., 1965, 87, 3554-3559. [all data]

Dorofeeva O.V., 1989
Dorofeeva O.V., Thermodynamic Properties of Gaseous Polycyclic Aromatic Hydrocarbons Containing Five-Membered Rings. Institute for High Temperatures, USSR Academy of Sciences, Preprint No.1-263 (in Russian), Moscow, 1989. [all data]

Finke, Messerly, et al., 1977
Finke, H.L.; Messerly, J.F.; Lee, S.H.; Osborn, A.G.; Douslin, D.R., Comprehensive thermodynamic studies of seven aromatic hydrocarbons, J. Chem. Thermodyn., 1977, 9, 937-956. [all data]

Sadowska, Stepniewska, et al., 1969
Sadowska, K.W.; Stepniewska, G.B.; Recko, W.M., Specific heat and enthalpy of fusion of acenaphthene and acenaphthylene, Przem. Chem., 1969, 48, 282-285. [all data]

Eibert, 1944
Eibert, J., Thesis Washington University (St. Louis), 1944. [all data]

Meot-Ner (Mautner), 1980
Meot-Ner (Mautner), M., Dimer Cations of Polycyclic Aromatics: Experimental Bonding Energies and Resonance Stabilization, J. Phys. Chem., 1980, 84, 21, 2724, https://doi.org/10.1021/j100458a012 . [all data]

Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A., Carbon Acidities of Aromatic Compounds, J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003 . [all data]

Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [all data]

Frye and Weitkamp, 1969
Frye, C.G.; Weitkamp, A.W., Equilibrium hydrogenations of multi-ring aromatics, J. Chem. Eng. Data, 1969, 14, 372-376. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D., Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons, Int. J. Mass Spectrom., 2000, 201, 283. [all data]

Mautner(Meot-Ner), 1980
Mautner(Meot-Ner), M., Ion thermochemistry of low volatility compounds in the gas phase. 3. Polycyclic aromatics: Ionization energies, proton, and hydrogen affinities. Extrapolations to graphite, J. Phys. Chem., 1980, 84, 2716. [all data]

Dewar, Haselbach, et al., 1970
Dewar, M.J.S.; Haselbach, E.; Worley, S.D., Calculated and observed ionization potentials of unsaturated polycyclic hydrocarbons; calculated heats of formation by several semiempirical s.c.f. m.o. methods, Proc. Roy. Soc. (London), 1970, A315, 431. [all data]

Kinoshita, 1962
Kinoshita, M., The absorption spectra of the molecular complexes of aromatic compounds with p-bromanil, Bull. Chem. Soc. Japan, 1962, 35, 1609. [all data]

Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K., Alkyl-induced, natural hypsochromic shifts of the ²A←²X and ²B←²X transitions of azulene and naphthalene radical cations, Nouv. J. Chim., 1976, 1, 105. [all data]

Boschi, Clar, et al., 1974
Boschi, R.; Clar, E.; Schmidt, W., Photoelectron spectra of polynuclear aromatics. III. The effect of nonplanarity in sterically overcrowded aromatic hydrocarbons, J. Chem. Phys., 1974, 60, 4406. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,solid	Constant pressure heat capacity of solid
  IE (evaluated)	Recommended ionization energy
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  T	Temperature
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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