Anthracene
- Formula: C14H10
- Molecular weight: 178.2292
- IUPAC Standard InChIKey: MWPLVEDNUUSJAV-UHFFFAOYSA-N
- CAS Registry Number: 120-12-7
- 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. - Isotopologues:
- Other names: Anthracin; Green Oil; Paranaphthalene; Tetra Olive N2G; Anthracene oil; p-Naphthalene; Anthracen; Coal tar pitch volatiles:anthracene; Sterilite hop defoliant
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Gas phase thermochemistry data
Go To: Top, 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 223. ± 10. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
41.38 | 50. | Dorofeeva O.V., 1988 | S(T) values calculated by [ Kudchadker S.A., 1979] are 3.6-4.1 J/mol*K greater than recommended ones. Cp(T) values from two calculations agree within 0.3 J/mol*K. Recommended values are also reproduced in the reference book [ Frenkel M., 1994].; GT |
61.44 | 100. | ||
87.80 | 150. | ||
118.55 | 200. | ||
167.75 | 273.15 | ||
184.7 ± 1.0 | 298.15 | ||
185.99 | 300. | ||
249.74 | 400. | ||
302.90 | 500. | ||
345.39 | 600. | ||
379.33 | 700. | ||
406.84 | 800. | ||
429.48 | 900. | ||
448.32 | 1000. | ||
464.17 | 1100. | ||
477.58 | 1200. | ||
489.01 | 1300. | ||
498.80 | 1400. | ||
507.22 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas 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:
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 | 121. ± 10. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -7061. ± 10. | kJ/mol | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 207.15 | J/mol*K | N/A | Goursot, Girdhar, et al., 1970 | DH |
S°solid,1 bar | 207.15 | J/mol*K | N/A | Goursot, Girdhar, et al., 1968 | DH |
S°solid,1 bar | 207.5 | J/mol*K | N/A | Huffman, Parks, et al., 1931 | Extrapolation below 90 K, 14.98 cal/mol*K.; DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
211.7 | 298.15 | Radomska and Radomski, 1980 | T = 180 to 430 K. Data given graphically. Cp calculated from equation.; DH |
210.50 | 298.15 | Goursot, Girdhar, et al., 1970 | T = 5 to 500 K.; DH |
210.50 | 298.15 | Goursot, Girdhar, et al., 1968 | T = 5 to 520 K. Only 6 points given; summary article.; DH |
217.5 | 298.15 | Ueberreiter and Orthmann, 1950 | T = 293 to 368 K. Equation only.; DH |
207.1 | 297.2 | Huffman, Parks, et al., 1931 | T = 94 to 297 K. Value is unsmoothed experimental datum.; DH |
221.8 | 298.15 | Hildebrand, Duschak, et al., 1917 | T = 293 to 593 K. From heat content data.; DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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)
LL - Sharon G. Lias and Joel F. Liebman
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 C14H10+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 7.439 ± 0.006 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 877.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 846.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.530 ± 0.020 | LPES | Ando, Mitsui, et al., 2007 | B |
0.5300 ± 0.0050 | LPES | Scheidt and Weinkauf, 1997 | B |
0.60 ± 0.10 | TDEq | Heinis, Chowdhury, et al., 1993 | ΔGea(343 K) = -13.2 kcal/mol; ΔSea = -1.1 eu.; B |
0.660 ± 0.060 | ECD | Ruoff, Kadish, et al., 1995 | Revised data, work of Becker and Chen, 1966; B |
0.570 ± 0.020 | ECD | Lyons, Morris, et al., 1968 | B |
0.5560 ± 0.0080 | ECD | Becker and Chen, 1966 | B |
<0.481 ± 0.039 | ECD | Wojnarovits and Foldiak, 1981 | EA is an upper limit: Chen and Wentworth, 1989.; B |
0.41998 | ECD | Wentworth and Becker, 1962 | B |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
869.4 | 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 |
---|---|---|
842.7 | Aue, Guidoni, et al., 2000 | Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM |
Ionization energy determinations
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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.
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]
Kudchadker S.A., 1979
Kudchadker S.A.,
Chemical thermodynamic properties of anthracene and phenathrene,
J. Chem. Thermodyn., 1979, 11, 1051-1059. [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]
Goursot, Girdhar, et al., 1970
Goursot, P.; Girdhar, H.L.; Westrum, E.F., Jr.,
Thermodynamics of polynuclear aromatic molecules. III. Heat capacities and enthalpies of fusion of anthracene,
J. Phys. Chem., 1970, 74, 2538-2541. [all data]
Goursot, Girdhar, et al., 1968
Goursot, P.; Girdhar, H.L.; Westrum, E.F., Jr.,
Mesure de la capacite calorifique de l'anthracene de 5 a 520K,
Compt. rend., 1968, C266, 949-950. [all data]
Huffman, Parks, et al., 1931
Huffman, H.M.; Parks, G.S.; Barmore, M.,
Thermal data on organic compounds. X. Further studies on the heat capacities, entropies and free energies of hydrocarbons,
J. Am. Chem. Soc., 1931, 53, 3876-3888. [all data]
Radomska and Radomski, 1980
Radomska, M.; Radomski, R.,
Calorimetric studies of binary systems of 1,3,5-trinitrobenzene with naphthalene, anthracene, and carbazole. I. Phase transitions and heat capacities of the pure components and charge-transfer complexes,
Thermochim. Acta, 1980, 40, 405-414. [all data]
Ueberreiter and Orthmann, 1950
Ueberreiter, K.; Orthmann, H.-J.,
Specifische Wärme, spezifisches Volumen, Temperatur- und Wärme-leittähigkeit einiger disubstituierter Benzole und polycyclischer Systeme,
Z. Natursforsch. 5a, 1950, 101-108. [all data]
Hildebrand, Duschak, et al., 1917
Hildebrand, J.H.; Duschak, A.D.; Foster, A.H.,
and Beebe, C.W. The specific heats and heats of fusion of triphenylmethane, anthraquinone and anthracene,
J. Am. Chem. Soc., 1917, 39, 2293-2297. [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]
Ando, Mitsui, et al., 2007
Ando, N.; Mitsui, M.; Nakajima, A.,
Comprehensive photoelectron spectroscopic study of anionic clusters of anthracene and its alkyl derivatives: Electronic structures bridging molecules to bulk,
J. Chem. Phys., 2007, 127, 23, 234305, https://doi.org/10.1063/1.2805185
. [all data]
Scheidt and Weinkauf, 1997
Scheidt, J.; Weinkauf, R.,
Photodetachment photoelectron spectroscopy of Mass Selected Anions: Anthracene and the Anthracene-H2O Cluster,
Chem. Phys. Lett., 1997, 266, 1-2, 201, https://doi.org/10.1016/S0009-2614(96)01512-6
. [all data]
Heinis, Chowdhury, et al., 1993
Heinis, T.; Chowdhury, S.; Kebarle, P.,
Electron Affinities of Naphthalene, Anthracene and Substituted Naphthalenes and Anthracenes,
Org. Mass Spectrom., 1993, 28, 4, 358, https://doi.org/10.1002/oms.1210280416
. [all data]
Ruoff, Kadish, et al., 1995
Ruoff, R.S.; Kadish, K.M.; Boulas, P.; Chen, E.C.M.,
The relationship between the electron affinities and half-wave reduction potentials of fullerenes, aromatic hydrocarbons, and metal complexes,
J. Phys. Chem., 1995, 99, 21, 8843, https://doi.org/10.1021/j100021a060
. [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]
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]
Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G.,
Electron capture detection of aromatic hydrocarbons,
J. Chromatogr. Sci., 1981, 206, 511. [all data]
Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E.,
Experimental Determination of Electron Affinities of Organic Molecules,
Mol. Cryst. Liq. Cryst., 1989, 171, 271. [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]
Hager and Wallace, 1988
Hager, J.W.; Wallace, S.C.,
Two-laser photoionization supersonic jet mass spectrometry of aromatic molecules,
Anal. Chem., 1988, 60, 5. [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]
Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H.,
Photoelectron spectra of acenes. Electronic structure and substituent effects,
Pure Appl. Chem., 1983, 55, 289. [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]
Streets and Williams, 1974
Streets, D.G.; Williams, T.A.,
Photoelectron spectroscopy of 9,10-dihaloanthracenes,
J. Electron Spectrosc. Relat. Phenom., 1974, 3, 71. [all data]
Koch, Otto, et al., 1973
Koch, E.E.; Otto, A.; Radler, K.,
The absorption spectrum of the anthracene molecule in the vacuum ultraviolet,
Chem. Phys. Lett., 1973, 21, 501. [all data]
Aihara and Inokuchi, 1973
Aihara, J.; Inokuchi, H.,
Ionization potentials of anthracene,
Chem. Lett., 1973, 421. [all data]
Eland, 1972
Eland, J.H.D.,
Photoelectron spectra and ionization potentials of aromatic hydrocarbons,
Int. J. Mass Spectrom. Ion Phys., 1972, 9, 214. [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]
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]
Boschi, Murrell, et al., 1972
Boschi, R.; Murrell, J.N.; Schmidt, W.,
Photoelectron spectra of polycyclic aromatic hydrocarbons,
Faraday Discuss. Chem. Soc., 1972, 54, 116. [all data]
Rowland, 1971
Rowland, C.G.,
Kinetic energy distributions of C12H8 fragment ions in the mass spectra of anthracene, phenanthrene and diphenylacetylene,
Intern. J. Mass Spectrom. Ion Phys., 1971, 7, 79. [all data]
Kitagawa, 1968
Kitagawa, T.,
Absorption spectra and photoionization of polycyclic aromatics in vacuum ultraviolet region,
J. Mol. Spectry., 1968, 26, 1. [all data]
Angus and Morris, 1966
Angus, J.A.; Morris, G.C.,
Ionization potential of the anthracene molecule from Rydberg absorption bands,
J.Mol. Spectry., 1966, 21, 310. [all data]
Kuroda, 1964
Kuroda, H.,
Ionization potentials of polycyclic aromatic hydrocarbons,
Nature, 1964, 201, 1214. [all data]
Finch, 1964
Finch, A.C.M.,
Charge-transfer spectra and the ionization energy of azulene,
J. Chem. Soc., 1964, 2272. [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]
Terenin, 1961
Terenin, A.,
Charge transfer in organic solids, induced by light,
Proc. Chem. Soc., London, 1961, 321. [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]
Wacks and Dibeler, 1959
Wacks, M.E.; Dibeler, V.H.,
Electron impact studies of aromatic hydrocarbons. I. Benzene, naphthalene, anthracene, and phenanthrene,
J. Chem. Phys., 1959, 31, 1557. [all data]
Foster, 1959
Foster, R.,
Ionization potentials of electron donors,
Nature (London), 1959, 183, 1253. [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]
Klasinc, Kovac, et al., 1978
Klasinc, L.; Kovac, B.; Schoof, S.; Gusten, H.,
Photoelectron spectroscopy of 9-substituted anthracenes,
Croat. Chem. Acta., 1978, 51, 307. [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]
Jongsma, Vermeer, et al., 1975
Jongsma, C.; Vermeer, H.; Bickelhaupt, F.; Schafer, W.; Schweig, A.,
10-methyl-9-phosphaanthracene,
Tetrahedron, 1975, 31, 2931. [all data]
Hush, Cheung, et al., 1975
Hush, N.S.; Cheung, A.S.; Hilton, P.R.,
Binding energies of π- and "lone pair"-levels in mono- and diaza-phenanthrenes and anthracenes: an He(I) photoelectron spectroscopic study,
J. Electron Spectrosc. Relat. Phenom., 1975, 7, 385. [all data]
Marschner and Goetz, 1974
Marschner, F.; Goetz, H.,
Korrelation zwischen photoelektronen- und elektronen-spektren. II. Untersuchung aromatischer π-systeme mit modifizierten PPP-SCF-CI-parametern,
Tetrahedron, 1974, 30, 3159. [all data]
Schafer, Schweig, et al., 1972
Schafer, W.; Schweig, A.; Bickelhaupt, F.; Vermeer, H.,
Photoelectron spectroscopy and conjugation. Direct proof of the unusual sequence of the two highest occupied π-molecular orbitals in the phosphorin (phosphabenzene) and the arsenin (arsabenzene) system,
Angew. Chem. Int. Ed. Engl., 1972, 11, 924. [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:
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) 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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