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
IUPAC Standard InChIKey: IFLREYGFSNHWGE-UHFFFAOYSA-N
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
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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:
Other data available:
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 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	81.9 ± 1.4	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
11.63	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
18.24	100.
26.346	150.
35.712	200.
50.631	273.15
55.77 ± 0.36	298.15
56.150	300.
75.406	400.
91.463	500.
104.29	600.
114.53	700.
122.81	800.
129.61	900.
135.25	1000.
139.99	1100.
143.99	1200.
147.39	1300.
150.30	1400.
152.80	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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	49.40 ± 0.72	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
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-2140.76 ± 0.32	kcal/mol	Ccb	Magnus, Hartmann, et al., 1951	Reanalyzed by Cox and Pilcher, 1970, Original value = -2140.86 ± 0.32 kcal/mol; Corresponding Δ_fHº_solid = 37.95 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	51.48	cal/mol*K	N/A	Wong and Westrum, 1980	DH

Constant pressure heat capacity of solid

C_p,solid (cal/mol*K)	Temperature (K)	Reference	Comment
56.55	298.15	Wong and Westrum, 1980	T = 5 to 350 K.; DH

Phase change data

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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

Quantity	Value	Units	Method	Reference	Comment
T_fus	613.15	K	N/A	Inokuchi, Shiba, et al., 1952	Uncertainty assigned by TRC = 2. K; TRC
T_fus	613.15	K	N/A	Inokuchi, 1951	Uncertainty assigned by TRC = 2. K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	25.38 ± 0.88	kcal/mol	CGC	Hanshaw, Nutt, et al., 2008	AC
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	32.48 (+0.1,-0.02)	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
Δ_subH°	34. ± 1.	kcal/mol	V	Kruif, 1980	ALS
Δ_subH°	34.3 ± 0.1	kcal/mol	TE,M	Kruif, 1980	Based on data from 419. to 446. K.; AC
Δ_subH°	29.8	kcal/mol	V	Wakayama and Inokuchi, 1967	ALS

Enthalpy of sublimation

Δ_subH (kcal/mol)	Temperature (K)	Method	Reference	Comment
29.83 ± 0.62	399. to 430.	ME	Oja, Chen, et al., 2009	AC
30.1 ± 2.2	429.	ME	Oja and Suuberg, 1998	Based on data from 386. to 472. K.; AC
30.23	383.	GS	Nass, Lenoir, et al., 1995	Based on data from 313. to 453. K.; AC
29.8 ± 1.	422.	ME	Wakayama and Inokuchi, 1967, 2	See also Pedley and Rylance, 1977.; AC
30.78	473.	HSA	Morris, 1965	Based on data from 433. to 493. K.; AC
31.69	468.	HSA	Fielding and MacKay, 1964	Based on data from 433. to 483. K.; AC
28.01	459.	ME	Inokuchi, Shiba, et al., 1952	See also Jones, 1960.; AC
29.7	293.	V	Magnus, Hartmann, et al., 1951	ALS

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Gas Chromatography

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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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Column type	Active phase	I	Reference	Comment
Capillary	SE-52	2426.	Beernaert, 1979	He, 50. C @ 5. min, 6. K/min; Column length: 33.3 m; Column diameter: 0.50 mm; T_end: 320. C
Capillary	SE-52	2425.	Carugno and Rossi, 1967	N2, 1.8 K/min; Column length: 65. m; Column diameter: 0.3 mm; T_start: 100. C; T_end: 300. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	Methyl Silicone	2395.	Oda, Ichikawa, et al., 1996	Program: 50C (2min) => 20C/min => 160C => 5C/min => 210C => 10C/min => 300C
Capillary	Methyl Silicone	2425.	Oda, Ichikawa, et al., 1996	Program: 50C (2min) => 20C/min => 160C => 5C/min => 210C => 10C/min => 300C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	SE-30	2386.	Pozhidaev, Berezkin, et al., 1987	He, 6. K/min; Column length: 25. m; Column diameter: 0.21 mm; T_start: 40. C; T_end: 280. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	Methyl Silicone	2436.	Oda, Yasuhara, et al., 1998	25. m/0.25 mm/0.25 μm, He; Program: 50 0C (2 min) 20 0C/min -> 160 0C 5 0C/min -> 210 0C 10 0C/min -> 300 0C

Lee's RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	Methyl Silicone	260.	403.9	Shlyakhov, 1984
Packed	Methyl Silicone	300.	405.0	Shlyakhov, 1984

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

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Column type	Active phase	I	Reference	Comment
Capillary	PE-5	403.5	Jamoussi, Kanzari, et al., 2007	20. m/0.18 mm/0.18 μm, 50. C @ 1.5 min, 8. K/min; T_end: 345. C
Capillary	HP-5	403.15	Pedersen, Durant, et al., 2005	30. m/0.25 mm/0.25 μm, Helium, 50. C @ 1.5 min, 6. K/min, 310. C @ 10. min
Capillary	HP-5	402.86	Marynowski, Pieta, et al., 2004	60. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 35. C; T_end: 300. C
Capillary	DB-5	407.3	Durlak, Biswas, et al., 1998	30. m/0.25 mm/0.25 μm, 15. K/min; T_start: 50. C; T_end: 300. C
Capillary	SE-54	403.52	Guillén, Blanco, et al., 1989	20. m/0.22 mm/0.20 μm, He, 4. K/min; T_start: 50. C; T_end: 300. C
Capillary	SE-52	408.30	Lee, Vassilaros, et al., 1979	12. m/0.3 mm/0.34 μm, He, 2. K/min; T_start: 50. C; T_end: 250. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	SE-54	401.28	Guillen, Iglesias, et al., 1992	Program: not specified
Capillary	OV-101	405.7	Tucminen, Wickstrom, et al., 1986	Program: not specified
Capillary	SE-52	403.51	Shlyakhov, 1984	Program: not specified
Capillary	SE-52	403.70	Shlyakhov, 1984	Program: not specified
Capillary	SE-52	403.89	Shlyakhov, 1984	Program: not specified
Capillary	SE-52	408.30	Shlyakhov, 1984	Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, 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]

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, 1980
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]

Inokuchi, Shiba, et al., 1952
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]

Inokuchi, 1951
Inokuchi, H., J. Chem. Soc. Jpn. Pure Chem. Sect., 1951, 72, 552. [all data]

Hanshaw, Nutt, et al., 2008
Hanshaw, William; Nutt, Marjorie; Chickos, James S., Hypothetical Thermodynamic Properties. Subcooled Vaporization Enthalpies and Vapor Pressures of Polyaromatic Hydrocarbons, J. Chem. Eng. Data, 2008, 53, 8, 1903-1913, https://doi.org/10.1021/je800300x . [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]

Wakayama and Inokuchi, 1967
Wakayama, N.; Inokuchi, H., Heats of sublimation of polycyclic aromatic hydrocarbons and their molecular packings, Bull. Chem. Soc. Jpn., 1967, 40, 2267. [all data]

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]

Beernaert, 1979
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]

Carugno and Rossi, 1967
Carugno, N.; Rossi, S., Evaluation of polynuclear hydrocarbons in cigarette smoke by glass capillary columns, J. Gas Chromatogr., 1967, 5, 2, 103-106, https://doi.org/10.1093/chromsci/5.2.103 . [all data]

Oda, Ichikawa, et al., 1996
Oda, J.; Ichikawa, S.; Mori, T., Analysis of polycyclic aromatic hydrocarbons in airborne particulates by capillary GC/MS method with programmed temperature relative retention index, Bunseki Kagaku, 1996, 45, 9, 825-835, https://doi.org/10.2116/bunsekikagaku.45.825 . [all data]

Pozhidaev, Berezkin, et al., 1987
Pozhidaev, V.M.; Berezkin, V.G.; Korolev, A.A.; Popova, T.P.; Pozhideava, Capillary chromatography of polycyclic aromatic hydrocarbons on a home-produced capillary column with immobilized stationary liquid phase SE-30, Zh. Anal. Khim., 1987, 62, 12, 2222-2226. [all data]

Oda, Yasuhara, et al., 1998
Oda, J.; Yasuhara, A.; Matsunaga, K.; Saito, Y., Identification of polycyclic aromatic hydrocarbons of the particulate accumulated in the tunnel duct of freeway and generation of their oxygenated derivatives, Jpn. J. Toxicol. Environ. Health, 1998, 44, 5, 334-351, https://doi.org/10.1248/jhs1956.44.334 . [all data]

Shlyakhov, 1984
Shlyakhov, A.F., Gas chromatography in organic geochemistry, Nedra, Moscow, 1984, 221. [all data]

Jamoussi, Kanzari, et al., 2007
Jamoussi, B.; Kanzari, F.; Hassine, B.B.; Abderrabba, A., Using Bezier curves for the calculation of retention indices of polycyclic aromatic hydrocarbons in the so-called Lee's scale in temperature-programmed gas chromatography with mass spectrometry detection, J. Chromatogr. Sci., 2007, 45, 1, 22-27, https://doi.org/10.1093/chromsci/45.1.22 . [all data]

Pedersen, Durant, et al., 2005
Pedersen, D.U.; Durant, J.L.; Taghizadeh, K.; Hemond, H.F.; Lafleur, A.L.; Cass, G.R., Human cell mutagenes in respirable airborne particles from the Northeastern United States. 2. Quantification of mutagenes and other organic compounds., Environ. Sci. Technol., 2005, 39, 24, 9547-9560, https://doi.org/10.1021/es050886c . [all data]

Marynowski, Pieta, et al., 2004
Marynowski, L.; Pieta, M.; Janeczek, J., Composition and source of polycyclic aromatic compounds in deposited dust from selected sites around the Upper Silesia, Poland, Geol. Q., 2004, 48, 2, 169-180. [all data]

Durlak, Biswas, et al., 1998
Durlak, S.K.; Biswas, P.; Shi, J.; Bernhard, M.J., Characterization of polycyclic aromatic hydrocarbon particulate and gaseous emissions from polystyrene combustion, Environ. Sci. Technol., 1998, 32, 15, 2301-2307, https://doi.org/10.1021/es9709031 . [all data]

Guillén, Blanco, et al., 1989
Guillén, M.D.; Blanco, J.; Bermejo, J.; Blanco, C.G., Temperature programmed retention indices of some PAHs on Capillary columns coated with OV-1701 and SE-54, J. Hi. Res. Chromatogr., 1989, 12, 8, 552-554, https://doi.org/10.1002/jhrc.1240120816 . [all data]

Lee, Vassilaros, et al., 1979
Lee, M.L.; Vassilaros, D.L.; White, C.M.; Novotny, M., Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons, Anal. Chem., 1979, 51, 6, 768-773, https://doi.org/10.1021/ac50042a043 . [all data]

Guillen, Iglesias, et al., 1992
Guillen, M.D.; Iglesias, M.J.; Dominguez, A.; Blanco, C.G., Polynuclear aromatic hydrocarbon retention indices on SE-54 stationary phase of the volatile components of a coal tar pitch. Relationships between chromatographic retention and thermal reactivity, J. Chromatogr., 1992, 591, 1-2, 287-295, https://doi.org/10.1016/0021-9673(92)80246-Q . [all data]

Tucminen, Wickstrom, et al., 1986
Tucminen, A.; Wickstrom, K.; Pyysalo, H., Determination of Polycyclic Aromatic Compounds by GLC-Selected Ion Monitoring (SIM) Technique, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 8, 469-471, https://doi.org/10.1002/jhrc.1240090813 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References

Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
C_p,solid	Constant pressure heat capacity of solid
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
T_fus	Fusion (melting) point
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
Δ_subH	Enthalpy of sublimation
Δ_subH°	Enthalpy of sublimation at standard conditions
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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