Naphthacene
- Formula: C18H12
- Molecular weight: 228.2879
- 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
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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References, Notes
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 342.6 ± 5.9 | kJ/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
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
48.65 | 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 |
76.30 | 100. | ||
110.23 | 150. | ||
149.42 | 200. | ||
211.84 | 273.15 | ||
233.4 ± 1.5 | 298.15 | ||
234.93 | 300. | ||
315.50 | 400. | ||
382.68 | 500. | ||
436.36 | 600. | ||
479.21 | 700. | ||
513.85 | 800. | ||
542.28 | 900. | ||
565.90 | 1000. | ||
585.71 | 1100. | ||
602.44 | 1200. | ||
616.67 | 1300. | ||
628.84 | 1400. | ||
639.30 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, References, Notes
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 206.7 ± 3.0 | kJ/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 |
ΔcH°solid | -8956.9 ± 1.3 | kJ/mol | Ccb | Magnus, Hartmann, et al., 1951 | Reanalyzed by Cox and Pilcher, 1970, Original value = -8957.4 ± 1.3 kJ/mol; Corresponding ΔfHºsolid = 158.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 215.4 | J/mol*K | N/A | Wong and Westrum, 1980 | DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
236.6 | 298.15 | Wong and Westrum, 1980 | T = 5 to 350 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References, Notes
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 613.15 | K | N/A | Inokuchi, Shiba, et al., 1952 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 613.15 | K | N/A | Inokuchi, 1951 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 106.2 ± 3.7 | kJ/mol | CGC | Hanshaw, Nutt, et al., 2008 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 135.9 (+0.5,-0.1) | kJ/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 |
ΔsubH° | 144. ± 5. | kJ/mol | V | Kruif, 1980 | ALS |
ΔsubH° | 143.7 ± 0.5 | kJ/mol | TE,M | Kruif, 1980 | Based on data from 419. to 446. K.; AC |
ΔsubH° | 125. | kJ/mol | V | Wakayama and Inokuchi, 1967 | ALS |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
124.8 ± 2.6 | 399. to 430. | ME | Oja, Chen, et al., 2009 | AC |
126.1 ± 9.0 | 429. | ME | Oja and Suuberg, 1998 | Based on data from 386. to 472. K.; AC |
126.5 | 383. | GS | Nass, Lenoir, et al., 1995 | Based on data from 313. to 453. K.; AC |
125. ± 4. | 422. | ME | Wakayama and Inokuchi, 1967, 2 | See also Pedley and Rylance, 1977.; AC |
128.8 | 473. | HSA | Morris, 1965 | Based on data from 433. to 493. K.; AC |
132.6 | 468. | HSA | Fielding and MacKay, 1964 | Based on data from 433. to 483. K.; AC |
117.2 | 459. | ME | Inokuchi, Shiba, et al., 1952 | See also Jones, 1960.; AC |
124. | 293. | V | Magnus, Hartmann, et al., 1951 | ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References, Notes
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 6.97 ± 0.05 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 905.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 876.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.0580 ± 0.0050 | LPES | Mitsui, Ando, et al., 2007 | B |
1.067 ± 0.043 | IMRE | Crocker, Wang, et al., 1993 | ΔGea(458 K) = -23.9 kcal/mol; ΔSea (estimated) = -1.5 eu (anthracene, Chowdhury, Heinis, et al., 1986); B |
0.880 ± 0.040 | ECD | Lyons, Morris, et al., 1968 | B |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
908.3 | 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 |
---|---|---|
884.1 | 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 |
---|---|---|---|
6.97 | EI | Stahl and Maquin, 1984 | LBLHLM |
6.9 ± 0.3 | EI | Shushan and Boyd, 1980 | LLK |
6.97 | PE | Schmidt, 1977 | LLK |
7.04 | PE | Clar and Schmidt, 1975 | LLK |
7.04 ± 0.04 | PE | Boschi, Clar, et al., 1974 | LLK |
7.01 | PE | Clark, Brogli, et al., 1972 | LLK |
7.0 ± 0.3 | EI | Wacks, 1964 | RDSH |
6.94 | CTS | Kuroda, 1964 | RDSH |
6.95 | CTS | Briegleb, 1964 | RDSH |
6.9 | PI | Terenin, 1961 | RDSH |
7.00 | CTS | Birks and Stifkin, 1961 | RDSH |
7.0 | CTS | Briegleb and Czekalla, 1959 | RDSH |
6.64 | CTS | Matsen, 1956 | RDSH |
6.97 ± 0.02 | PE | Schmidt, 1977 | Vertical value; LLK |
7.01 | PE | Brogli and Heilbronner, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C16H10+ | 15.5 ± 0.5 | C2H2 | EI | Shushan and Boyd, 1980 | LLK |
C18H11+ | 14.5 ± 0.5 | H | EI | Shushan and Boyd, 1980 | LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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]
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]
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]
Chowdhury, Heinis, et al., 1986
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,
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. [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]
Stahl and Maquin, 1984
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]
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]
Schmidt, 1977
Schmidt, W.,
Photoelectron spectra of polynuclear aromatics. V. Correlations with ultraviolet absorption spectra in the catacondensed series,
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Clar and Schmidt, 1975
Clar, E.; Schmidt, W.,
Correlations btween photoelectron and ultraviolet absorption spectra of polycyclic hydrocarbons and the number of aromatic sextets,
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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,
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Clark, Brogli, et al., 1972
Clark, P.A.; Brogli, F.; Heilbronner, E.,
The π-orbital energies of the acenes,
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Wacks, 1964
Wacks, M.E.,
Electron-impact studies of aromatic hydrocarbons. II. Naphthacene, naphthaphene, chrysene, triphenylene, and pyrene,
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Kuroda, 1964
Kuroda, H.,
Ionization potentials of polycyclic aromatic hydrocarbons,
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Briegleb, 1964
Briegleb, G.,
Electron affinity of organic molecules,
Angew. Chem. Intern. Ed., 1964, 3, 617. [all data]
Terenin, 1961
Terenin, A.,
Charge transfer in organic solids, induced by light,
Proc. Chem. Soc., London, 1961, 321. [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,
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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, Phase change data, Gas phase ion energetics data, 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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