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, Gas phase ion energetics data, IR Spectrum, 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 | 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
Cp,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. |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, IR Spectrum, 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) | 216.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 209.5 | kcal/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 (kcal/mol) | Reference | Comment |
---|---|---|
217.1 | 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) (kcal/mol) | Reference | Comment |
---|---|---|
211.3 | 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 |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References, Notes
Data compiled by: Coblentz Society, Inc.
- SOLID (2.0% 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
- SOLID (SPLIT MULL), FLUOROLUBE FOR 3800-1330 CM-1, NUJOL FOR 1330-400 CM-1 $$ SPECTRAL FEATURE AT 1994 CM-1 IS AN ARTIFACT CAUSED BY GRATING CHANGE; DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
- SOLID (SPLIT MULL, FLUOROLUBE FOR 3800-1333 AND NUJOL FOR 1333-400 CM -1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR 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]
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,
J. Phys. Chem., 1968, 72, 10, 3677, https://doi.org/10.1021/j100856a056
. [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,
J. Chem. Phys., 1977, 66, 828. [all data]
Clar and Schmidt, 1975
Clar, E.; Schmidt, W.,
Correlations btween photoelectron and ultraviolet absorption spectra of polycyclic hydrocarbons and the number of aromatic sextets,
Tetrahedron, 1975, 31, 2263. [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]
Clark, Brogli, et al., 1972
Clark, P.A.; Brogli, F.; Heilbronner, E.,
The π-orbital energies of the acenes,
Helv. Chim. Acta, 1972, 55, 1415. [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]
Kuroda, 1964
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]
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,
J. Chem. Phys., 1956, 24, 602. [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, Gas phase ion energetics data, IR 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 ΔfH°gas Enthalpy of formation of gas at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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