Naphthacene

• Formula: C₁₈H₁₂
• Molecular weight: 228.2879
• IUPAC Standard InChI: InChI=1S/C18H12/c1-2-6-14-10-18-12-16-8-4-3-7-15(16)11-17(18)9-13(14)5-1/h1-12H Copy

  
• IUPAC Standard InChIKey: IFLREYGFSNHWGE-UHFFFAOYSA-N Copy
• CAS Registry Number: 92-24-0
• 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.
• Other names: Tetracene; Benz[b]anthracene; Chrysogen; Methacene; Rubene; Tetracen; 2,3-Benzanthrene; 2,3-Benzanthracene; Benzo[b]anthracene; Tetracene (hydrocarbon)
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Data at other public NIST sites:
  • X-ray Photoelectron Spectroscopy Database, version 5.0
  • 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.
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

Phase change 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of sublimation

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:
MM - Michael M. Meot-Ner (Mautner)
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

View reactions leading to C₁₈H₁₂⁺ (ion structure unspecified)

Electron affinity determinations

Proton affinity at 298K

Gas basicity at 298K

Ionization energy determinations

Appearance energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLID (2.0% IN KBr PELLET); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• SOLID (SPLIT MULL), FLUOROLUBE FOR 3800-1330 CM^-1, NUJOL FOR 1330-400 CM^-1 $$ SPECTRAL FEATURE AT 1994 CM^-1 IS AN ARTIFACT CAUSED BY GRATING CHANGE; DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution
• SOLID (SPLIT MULL, FLUOROLUBE FOR 3800-1333 AND NUJOL FOR 1333-400 CM ^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Mass spectrum (electron ionization)

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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Gas Chromatography

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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Lee's RI, non-polar column, isothermal

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Lee's RI, non-polar column, temperature ramp

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Lee's RI, non-polar column, custom temperature program

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
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Dorofeeva O.V., On calculation of thermodynamic properties of polycyclic aromatic hydrocarbons, Thermochim. Acta, 1986, 102, 59-66. [all data]

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Moiseeva N.F., Development of Benson group additivity method for estimation of ideal gas thermodynamic properties of polycyclic aromatic hydrocarbons, Thermochim. Acta, 1989, 153, 77-85. [all data]

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Magnus, A.; Hartmann, H.; Becker, F., Verbrennungswarmen und resonanzenergien von mehrkernigen aromatischen kohlenwasserstoffen, Z. Phys. Chem., 1951, 197, 75-91. [all data]

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Wong, W.K.; Westrum, E.F., Jr., Thermodynamics of polynuclear aromatic molecules. II. Low temperature thermal properties of perylene, coronene, and naphthacene, Mol. Cryst. Liq. Cryst., 1980, 61, 207-228. [all data]

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Inokuchi, Hiroo; Shiba, Sukekuni; Handa, Takashi; Akamatu, Hideo, Heats of Sublimation of Condensed Polynuclear Aromatic Hydrocarbons, Bull. Chem. Soc. Jpn., 1952, 25, 5, 299-302, https://doi.org/10.1246/bcsj.25.299 . [all data]

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Oja, Chen, et al., 2009
Oja, Vahur; Chen, Xu; Hajaligol, Mohammad R.; Chan, W. Geoffrey, Sublimation Thermodynamic Parameters for Cholesterol, Ergosterol, β-Sitosterol, and Stigmasterol, J. Chem. Eng. Data, 2009, 54, 3, 730-734, https://doi.org/10.1021/je800395m . [all data]

Oja and Suuberg, 1998
Oja, Vahur; Suuberg, Eric M., Vapor Pressures and Enthalpies of Sublimation of Polycyclic Aromatic Hydrocarbons and Their Derivatives, J. Chem. Eng. Data, 1998, 43, 3, 486-492, https://doi.org/10.1021/je970222l . [all data]

Nass, Lenoir, et al., 1995
Nass, Karen; Lenoir, Dieter; Kettrup, Antonius, Calculation of the Thermodynamic Properties of Polycyclic Aromatic Hydrocarbons by an Incremental Procedure, Angew. Chem. Int. Ed. Engl., 1995, 34, 16, 1735-1736, https://doi.org/10.1002/anie.199517351 . [all data]

Wakayama and Inokuchi, 1967, 2
Wakayama, Nobuko; Inokuchi, Hiroo, Heats of Sublimation of Polycyclic Aromatic Hydrocarbons and Their Molecular Packings, Bull. Chem. Soc. Jpn., 1967, 40, 10, 2267-2271, https://doi.org/10.1246/bcsj.40.2267 . [all data]

Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J., , Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brighton, 1977. [all data]

Morris, 1965
Morris, G.C., The intensity of absorption of naphthacene vapor from 20 000 to 54 000 cm-1, Journal of Molecular Spectroscopy, 1965, 18, 1, 42-50, https://doi.org/10.1016/0022-2852(65)90059-7 . [all data]

Fielding and MacKay, 1964
Fielding, PE; MacKay, AG, Vapour phase spectrum and enthalpy of sublimation of naphthacene, Aust. J. Chem., 1964, 17, 11, 1288-621, https://doi.org/10.1071/CH9641288 . [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [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]

Mitsui, Ando, et al., 2007
Mitsui, M.; Ando, N.; Nakajima, A., Mass spectrometry and photoelectron spectroscopy of tetracene cluster anions, (Tetracene)(n)(-) (n=1-100): Evidence for the highly localized nature of polarization in a cluster analogue of o, J. Phys. Chem. A, 2007, 111, 39, 9644-9648, https://doi.org/10.1021/jp076134h . [all data]

Crocker, Wang, et al., 1993
Crocker, L.; Wang, T.B.; Kebarle, P., Electron Affinities of Some Polycyclic Aromatic Hydrocarbons, Obtained from Electron-Transfer Equilibria, J. Am. Chem. Soc., 1993, 115, 17, 7818, https://doi.org/10.1021/ja00070a030 . [all data]

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Chowdhury, S.; Heinis, T.; Grimsrud, E.P.; Kebarle, P., Entropy Changes and Electron Affinities from Gas-Phase Electron Transfer Equilibria: A^- + B = A + B^-, J. Phys. Chem., 1986, 90, 12, 2747, https://doi.org/10.1021/j100403a037 . [all data]

Lyons, Morris, et al., 1968
Lyons, L.E.; Morris, G.C.; Warren, L.J., Electron Affinities and the Electron Capture Method for Aromatic Hydrocarbons, J. Phys. Chem., 1968, 72, 10, 3677, https://doi.org/10.1021/j100856a056 . [all data]

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Stahl, D.; Maquin, F., Charge-stripping mass spectrometry of molecular ions from polyacenes and molecular orbital theory, Chem. Phys. Lett., 1984, 108, 613. [all data]

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Shushan, B.; Boyd, R.K., Unimolecular and collision induced fragmentations of molecular ions of polycyclic aromatic hydrocarbons, Org. Mass Spectrom., 1980, 15, 445. [all data]

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Schmidt, W., Photoelectron spectra of polynuclear aromatics. V. Correlations with ultraviolet absorption spectra in the catacondensed series, J. Chem. Phys., 1977, 66, 828. [all data]

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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]

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Wacks, M.E., Electron-impact studies of aromatic hydrocarbons. II. Naphthacene, naphthaphene, chrysene, triphenylene, and pyrene, J. Chem. Phys., 1964, 41, 1661. [all data]

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Kuroda, H., Ionization potentials of polycyclic aromatic hydrocarbons, Nature, 1964, 201, 1214. [all data]

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Birks, J.B.; Stifkin, M.A., π-Electronic excitation and ionization energies of condensed ring aromatic hydrocarbons, Nature, 1961, 191, 761. [all data]

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Briegleb, G.; Czekalla, J., Die Bestimmung von lonisierungsenergien aus den Spektren von Elektronenubergangskomplexen, Z.Elektrochem., 1959, 63, 6. [all data]

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Matsen, F.A., Electron affinities, methyl affinities, and ionization energies of condensed ring aromatic hydrocarbons, J. Chem. Phys., 1956, 24, 602. [all data]

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Beernaert, H., Gas Chromatographic Analysis of Polyclylic Aromatic Hydrocarbons, J. Chromatogr., 1979, 173, 1, 109-118, https://doi.org/10.1016/S0021-9673(01)80450-7 . [all data]

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Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Cp,solid	Constant pressure heat capacity of solid
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  Tfus	Fusion (melting) point
  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
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH°	Enthalpy of vaporization at standard conditions

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