Benzo[c]phenanthrene

Formula: C₁₈H₁₂
Molecular weight: 228.2879
IUPAC Standard InChI: InChI=1S/C18H12/c1-3-7-16-13(5-1)9-11-15-12-10-14-6-2-4-8-17(14)18(15)16/h1-12H
IUPAC Standard InChIKey: TUAHORSUHVUKBD-UHFFFAOYSA-N
CAS Registry Number: 195-19-7
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: 3,4-Benzophenanthrene; Benzo-3,4-phenanthrene; Tetrahelicene; 3,4-Benzphenanthrene
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	69.60	kcal/mol	Review	Roux, Temprado, et al., 2008	There are insufficient literature values to properly evaluated the data and measurements are of low quality and/or there is substantial disagreement with values predicted using thermochemical cycles or estimation methods (trends).; DRB

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
11.89	50.	Dorofeeva O.V., 1988	Recommended values were calculated statistically mechanically using force field approximation for polycyclic aromatic hydrocarbons to estimate the needed vibrational frequencies (see also [ Dorofeeva O.V., 1986, Moiseeva N.F., 1989]). These functions are reproduced in the reference book [ Frenkel M., 1994].; GT
18.58	100.
26.781	150.
36.224	200.
51.119	273.15
56.23 ± 0.36	298.15
56.609	300.
75.750	400.
91.716	500.
104.48	600.
114.68	700.
122.93	800.
129.70	900.
135.33	1000.
140.05	1100.
144.04	1200.
147.43	1300.
150.33	1400.
152.83	1500.

Condensed phase thermochemistry data

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Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	44.19 ± 0.72	kcal/mol	Review	Roux, Temprado, et al., 2008	There are insufficient literature values to properly evaluate the data and insufficient information to construct thermochemical cycles or estimate values for comparison, and one must rely solely upon reported uncertainities and the quality of the measurements. In general, the evaluated uncertainty limits are on the order of (3 to 9) kJ/mol.; DRB
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-2147.00 ± 0.45	kcal/mol	Ccb	Magnus, Hartmann, et al., 1951	Reanalyzed by Cox and Pilcher, 1970, Original value = -2147.10 ± 0.45 kcal/mol; Corresponding Δ_fHº_solid = 44.19 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Gas phase ion energetics data

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Data compiled as indicated in comments:
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

EA (eV)	Method	Reference	Comment
0.5450 ± 0.0080	ECD	Becker and Chen, 1966	B
0.33	ECD	Wentworth and Becker, 1962	B

Ionization energy determinations

IE (eV)	Method	Reference	Comment
7.86	CTS	Briegleb, 1964	RDSH
7.76	CTS	Matsen, 1956	RDSH
7.60 ± 0.02	PE	Schmidt, 1977	Vertical value; LLK
7.60	PE	Clar and Schmidt, 1976	Vertical value; LLK
7.62	PE	Brogli and Heilbronner, 1972	Vertical value; LLK

References

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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]

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]

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

Notes

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Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
EA	Electron affinity
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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