Triphenylene

Formula: C₁₈H₁₂
Molecular weight: 228.2879
IUPAC Standard InChI: InChI=1S/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H
IUPAC Standard InChIKey: SLGBZMMZGDRARJ-UHFFFAOYSA-N
CAS Registry Number: 217-59-4
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: Benzo[l]phenanthrene; Isochrysene; 1,2,3,4-Dibenznaphthalene; 9,10-Benzophenanthrene; 9,10-Benzphenanthrene
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Gas phase thermochemistry data

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

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	270.1 ± 4.4	kJ/mol	Review	Roux, Temprado, et al., 2008	There are sufficient literature values to make a qualified recommendation where the suggested value is in good agreement with values predicted using thermochemical cycles or from reliable estimates. In general, the evaluated uncertainty limits are on the order of (2 to 4) kJ/mol.; DRB

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
48.55	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
79.65	100.
114.46	150.
153.60	200.
215.30	273.15
236.5 ± 2.0	298.15
238.10	300.
317.76	400.
384.32	500.
437.57	600.
480.13	700.
514.58	800.
542.86	900.
566.37	1000.
586.10	1100.
602.77	1200.
616.95	1300.
629.08	1400.
639.51	1500.

Condensed phase thermochemistry data

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	150. ± 2.9	kJ/mol	Review	Roux, Temprado, et al., 2008	There are sufficient literature values to make a qualified recommendation where the suggested value is in good agreement with values predicted using thermochemical cycles or from reliable estimates. In general, the evaluated uncertainty limits are on the order of (2 to 4) kJ/mol.; DRB
Δ_fH°_solid	151.8 ± 1.5	kJ/mol	Ccb	Douslin, Scott, et al., 1976	crystal phase; see Good, 1978; ALS
Δ_fH°_solid	141.0 ± 0.46	kJ/mol	Ccr	Westrum and Wong, 1967	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-8950.0 ± 1.2	kJ/mol	Ccb	Douslin, Scott, et al., 1976	crystal phase; see Good, 1978; Corresponding Δ_fHº_solid = 151.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-8939.24 ± 0.46	kJ/mol	Ccr	Westrum and Wong, 1967	Corresponding Δ_fHº_solid = 141.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-8945.4 ± 2.2	kJ/mol	Ccb	Magnus, Hartmann, et al., 1951	Reanalyzed by Cox and Pilcher, 1970, Original value = -8945.9 ± 2.2 kJ/mol; Corresponding Δ_fHº_solid = 147.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	254.68	J/mol*K	N/A	Wong and Westrum, 1971	DH

Constant pressure heat capacity of solid

C_p,solid (J/mol*K)	Temperature (K)	Reference	Comment
259.20	298.15	Wong and Westrum, 1971	T = 5 to 514 K.; DH

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes

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)

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	7.87 ± 0.02	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	819.2	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	791.2	kJ/mol	N/A	Hunter and Lias, 1998	HL

Electron affinity determinations

EA (eV)	Method	Reference	Comment
0.2850 ± 0.0080	ECD	Becker and Chen, 1966	B
0.13998	ECD	Wentworth and Becker, 1962	B

Proton affinity at 298K

Proton affinity (kJ/mol)	Reference	Comment
818.0	Aue, Guidoni, et al., 2000	Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol)	Reference	Comment
792.9	Aue, Guidoni, et al., 2000	Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.0 ± 0.2	EI	Shushan and Boyd, 1980	LLK
7.84 ± 0.05	EQ	Mautner(Meot-Ner), 1980	LLK
7.89 ± 0.04	PE	Boschi, Clar, et al., 1974	LLK
7.84 ± 0.01	PE	Dewar and Goodman, 1972	LLK
8.2 ± 0.3	EI	Wacks, 1964	RDSH
8.17	CTS	Briegleb, 1964	RDSH
8.08	CTS	Kinoshita, 1962	RDSH
8.1	CTS	Briegleb, Czekalla, et al., 1961	RDSH
8.09	CTS	Birks and Stifkin, 1961	RDSH
7.95	CTS	Briegleb and Czekalla, 1959	RDSH
8.13	CTS	Matsen, 1956	RDSH
7.88 ± 0.02	PE	Schmidt, 1977	Vertical value; LLK
7.88	PE	Clar and Schmidt, 1976	Vertical value; LLK
7.86	PE	Brogli and Heilbronner, 1972	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₁₆H₁₀⁺	16.3 ± 0.3	C₂H₂	EI	Shushan and Boyd, 1980	LLK
C₁₈H₁₁⁺	15.4 ± 0.3	H	EI	Shushan and Boyd, 1980	LLK

References

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

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]

Douslin, Scott, et al., 1976
Douslin, D.R.; Scott, D.W.; Good, W.D.; Osborn, A.G., Thermodynamic properties of organic compounds and thermodynamic properties of fluids, Gov. Rep. Announce. Index U.S., 1976, 76, 97. [all data]

Good, 1978
Good, W.D., The enthalpies of formation of some bridged-ring polynuclear aromatic hydrocarbons, J. Chem. Thermodyn., 1978, 10, 553-558. [all data]

Westrum and Wong, 1967
Westrum, E.F., Jr.; Wong, S., Strain energies and thermal properties of globular and polynuclear aromatic molecules, AEC Rept. Coo-1149-92, Contract AT(11-1)-1149, 1967, 1-7. [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]

Wong and Westrum, 1971
Wong, W-K.; Westrum, E.F., Jr., Thermodynamics of polynuclear aromatic molecules. I. Heat capacities and enthalpies of fusion of pyrene, flouranthene, and triphenylene, J. Chem. Thermodynam., 1971, 3, 105-124. [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]

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]

Shushan and Boyd, 1980
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]

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]

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]

Dewar and Goodman, 1972
Dewar, M.J.S.; Goodman, D.W., Photoelectron spectra of molecules. Part 5.--Polycyclic aromatic hydrocarbons, J. Chem. Soc. Faraday Trans. 2, 1972, 68, 1784. [all data]

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

Briegleb and Czekalla, 1959
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]

Notes

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

Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
C_p,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)
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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