Chrysene

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

  
• IUPAC Standard InChIKey: WDECIBYCCFPHNR-UHFFFAOYSA-N Copy
• CAS Registry Number: 218-01-9
• 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:
  • Chrysene-D12
• Other names: Benzo[a]phenanthrene; 1,2-Benzophenanthrene; 1,2-Benzphenanthrene; Benz(a)phenanthrene; 1,2,5,6-Dibenzonaphthalene; Rcra waste number U050; Crysene
• 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
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas Chromatography
• Data at other public NIST sites:
  • 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

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:
BS - Robert L. Brown and Stephen E. Stein
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
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Enthalpy of vaporization

Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

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 by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

C₁₈H₁₂⁺ +  = (C₁₈H₁₂⁺ • )

By formula: C₁₈H₁₂⁺ + C₁₈H₁₂ = (C₁₈H₁₂⁺ • C₁₈H₁₂)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₁₈H₁₃⁺ +  = (C₁₈H₁₃⁺ • )

By formula: C₁₈H₁₃⁺ + C₁₈H₁₂ = (C₁₈H₁₃⁺ • C₁₈H₁₂)

Free energy of reaction

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)
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

Ion clustering 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 by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C₁₈H₁₂⁺ +  = (C₁₈H₁₂⁺ • )

By formula: C₁₈H₁₂⁺ + C₁₈H₁₂ = (C₁₈H₁₂⁺ • C₁₈H₁₂)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₁₈H₁₃⁺ +  = (C₁₈H₁₃⁺ • )

By formula: C₁₈H₁₃⁺ + C₁₈H₁₂ = (C₁₈H₁₃⁺ • C₁₈H₁₂)

Free energy of reaction

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLID (1.0% 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

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

• gas; HP-GC/MS/IRD

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

UV/Visible spectrum

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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

Dorofeeva O.V., 1988
Dorofeeva O.V., Thermodynamic Properties of Polycyclic Aromatic Hydrocarbons in the Gaseous Phase. Institute for High Temperatures, USSR Academy of Sciences, Preprint No.1-238 (in Russian), Moscow, 1988. [all data]

Dorofeeva O.V., 1986
Dorofeeva O.V., On calculation of thermodynamic properties of polycyclic aromatic hydrocarbons, Thermochim. Acta, 1986, 102, 59-66. [all data]

Moiseeva N.F., 1989
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]

Frenkel M., 1994
Frenkel M., Thermodynamics of Organic Compounds in the Gas State, Vol. I, II, Thermodynamics Research Center, College Station, Texas, 1994, 1994. [all data]

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

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Casellato, Vecchi, et al., 1973
Casellato, F.; Vecchi, C.; Girell, A., Differential calorimetric study of polycyclic aromatic hydrocarbons, Thermochim. Acta, 1973, 6, 4, 361, https://doi.org/10.1016/0040-6031(73)87003-0 . [all data]

Sangster and Irvine, 1956
Sangster, R.C.; Irvine, J.W., Study of Organic Scintillators, J. Chem. Phys., 1956, 24, 670. [all data]

Schuyer, Blom, et al., 1953
Schuyer, J.; Blom, L.; Van Krevelen, D.W., Molar refraction of condensed aromatic compounds., Trans. Faraday Soc., 1953, 49, 1391. [all data]

Jones and Neuworth, 1944
Jones, R.C.; Neuworth, M.B., The Ultraviolet Absorption Spectra of Hydrocarbon-Trinitrobenzene Complexes, J. Am. Chem. Soc., 1944, 66, 1497. [all data]

Baxter and Hale, 1936
Baxter, G.P.; Hale, A.H., A Revision of the Atomic Weight of Carbon, J. Am. Chem. Soc., 1936, 58, 510. [all data]

Zhao, Unhannanant, et al., 2008
Zhao, Hui; Unhannanant, Patamaporn; Hanshaw, William; Chickos, James S., Enthalpies of Vaporization and Vapor Pressures of Some Deuterated Hydrocarbons. Liquid-Vapor Pressure Isotope Effects, J. Chem. Eng. Data, 2008, 53, 7, 1545-1556, https://doi.org/10.1021/je800091s . [all data]

Haftka, Parsons, et al., 2006
Haftka, Joris J.H.; Parsons, John R.; Govers, Harrie A.J., Supercooled liquid vapour pressures and related thermodynamic properties of polycyclic aromatic hydrocarbons determined by gas chromatography, Journal of Chromatography A, 2006, 1135, 1, 91-100, https://doi.org/10.1016/j.chroma.2006.09.050 . [all data]

Kruif, 1980
Kruif, C.G., Enthalpies of sublimation and vapour pressures of 11 polycyclic hydrocarbons, J. Chem. Thermodyn., 1980, 12, 243-248. [all data]

Lei, Chankalal, et al., 2002
Lei, Ying Duan; Chankalal, Raymond; Chan, Anita; Wania, Frank, Supercooled Liquid Vapor Pressures of the Polycyclic Aromatic Hydrocarbons, J. Chem. Eng. Data, 2002, 47, 4, 801-806, https://doi.org/10.1021/je0155148 . [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
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]

Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Hoyer and Peperle, 1958
Hoyer, H.; Peperle, W., Z. Elektrochem., 1958, 62, 61. [all data]

Hoyer and Peperle, 1958, 2
Hoyer, H.; Peperle, W., Dampfdrunkmessungen an organischen substanzen und ihre sublimationswarmen, Z. Electrochem., 1958, 62, 61-66. [all data]

Kestens, Auclair, et al., 2010
Kestens, Vikram; Auclair, Guy; Drozdzewska, Katarzyna; Held, Andrea; Roebben, Gert; Linsinger, Thomas, Thermodynamic property values of selected polycyclic aromatic hydrocarbons measured by differential scanning calorimetry, J Therm Anal Calorim, 2010, 99, 1, 245-261, https://doi.org/10.1007/s10973-009-0440-6 . [all data]

Casellato, Vecchi, et al., 1973, 2
Casellato, F.; Vecchi, C.; Girelli, A.; Casu, B., Differential calorimetric study of polycyclic aromatic hydrocarbons, Thermochimica Acta, 1973, 6, 4, 361-368, https://doi.org/10.1016/0040-6031(73)87003-0 . [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]

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]

Tschurl and Boesl, 2006
Tschurl, M.; Boesl, U., Photodetachment-photoelectron spectroscopy of jet-cooled chrysene, Int. J. Mass Spectrom., 2006, 249, 364-369, https://doi.org/10.1016/j.ijms.2005.11.024 . [all data]

Becker and Chen, 1966
Becker, R.S.; Chen, E., Extension of Electron Affinities and Ionization Potentials of Aromatic Hydrocarbons, J. Chem. Phys., 1966, 45, 7, 2403, https://doi.org/10.1063/1.1727954 . [all data]

Wentworth and Becker, 1962
Wentworth, W.E.; Becker, R.S., Potential Method for the Determination of Electron Affinities of Molecules: Application to Some Aromatic Hydrocarbons., J. Am. Chem. Soc., 1962, 84, 22, 4263, https://doi.org/10.1021/ja00881a014 . [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]

Shahbaz, Akiyama, et al., 1981
Shahbaz, M.; Akiyama, I.; LeBreton, P., Ultraviolet photoelectron studies of methyl substituted chrysenes, Biochem. Biophys. Res. Commun., 1981, 103, 25. [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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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]

Boschi, Murrell, et al., 1972
Boschi, R.; Murrell, J.N.; Schmidt, W., Photoelectron spectra of polycyclic aromatic hydrocarbons, Faraday Discuss. Chem. Soc., 1972, 54, 116. [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]

Briegleb, 1964
Briegleb, G., Electron affinity of organic molecules, Angew. Chem. Intern. Ed., 1964, 3, 617. [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]

Briegleb, Czekalla, et al., 1961
Briegleb, G.; Czekalla, J.; Reuss, G., Mesomeriemomente und Elektronenuberfuhrungsbanden von Elektronen-donator-akzeptor-komplexen des Chloranils und Tetracyanathylens mit aromatischen Kohlenwasserstoffen, Z. Phys. Chem. (Neue Folge), 1961, 30, 333. [all data]

Birks and Stifkin, 1961
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]

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

Schmidt, 1977
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]

Clar and Schmidt, 1976
Clar, E.; Schmidt, W., Correlations between photoelectron and phosphorescence spectra of polycyclic hydrocarbons, Tetrahedron, 1976, 32, 2563. [all data]

Brogli and Heilbronner, 1972
Brogli, F.; Heilbronner, E., The photoelectron spectra of benzenoid hydrocarbons C₁₈H₁₂, Angew. Chem. Int. Ed. Engl., 1972, 11, 538. [all data]

Badger, Jamieson, et al., 1965
Badger, G.M.; Jamieson, N.C.; Lewis, G.E., Photochemical reactions of azo compounds. IV. Further photochemical cyclodehydrogenations, Aust. J. Chem., 1965, 18, 190-198. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  T	Temperature
  Tboil	Boiling point
  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
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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