Perylene
- Formula: C20H12
- Molecular weight: 252.3093
- IUPAC Standard InChI: InChI=1S/C20H12/c1-5-13-6-2-11-17-18-12-4-8-14-7-3-10-16(20(14)18)15(9-1)19(13)17/h1-12H
- IUPAC Standard InChIKey: CSHWQDPOILHKBI-UHFFFAOYSA-N
- CAS Registry Number: 198-55-0
- 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. - Isotopologues:
- Other names: Peri-Dinaphthalene; Dibenz[de,kl]anthracene; Perilene; α-Perylene
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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.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 318.3 ± 3.7 | 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 |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 47.53 | 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 |
| 80.23 | 100. | ||
| 119.96 | 150. | ||
| 164.18 | 200. | ||
| 232.28 | 273.15 | ||
| 255.4 ± 2.5 | 298.15 | ||
| 257.13 | 300. | ||
| 343.29 | 400. | ||
| 414.92 | 500. | ||
| 472.09 | 600. | ||
| 517.61 | 700. | ||
| 554.33 | 800. | ||
| 584.35 | 900. | ||
| 609.22 | 1000. | ||
| 630.01 | 1100. | ||
| 647.53 | 1200. | ||
| 662.39 | 1300. | ||
| 675.09 | 1400. | ||
| 685.98 | 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 | 182.4 ± 2.7 | 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 |
| ΔfH°solid | 182.7 ± 0.46 | kJ/mol | Ccr | Westrum and Wong, 1967 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -9767.97 ± 0.46 | kJ/mol | Ccr | Westrum and Wong, 1967 | Corresponding ΔfHºsolid = 182.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -9754. ± 61. | kJ/mol | Ccb | Pongratz and Griengl, 1929 | At 288 K; Corresponding ΔfHºsolid = 168.65 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 264.6 | 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 |
|---|---|---|---|
| 274.9 | 298.15 | Wong and Westrum, 1980 | T = 5 to 575 K.; 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
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 6.960 ± 0.001 | eV | N/A | N/A | L |
| Quantity | Value | Units | Method | Reference | Comment |
| Proton affinity (review) | 888.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 859.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 0.9730 ± 0.0050 | LPES | Scheidt and Weinkauf, 1997 | B |
| 0.993 ± 0.043 | IMRE | Crocker, Wang, et al., 1993 | ΔGea(425 K) = -22.3 kcal/mol; ΔSea (estimated) = -1.5 eu (anthracene, Chowdhury, Heinis, et al., 1986); B |
| 0.35 ± 0.10 | CIDC | Chen and Cooks, 1995 | B |
Proton affinity at 298K
| Proton affinity (kJ/mol) | Reference | Comment |
|---|---|---|
| 887.4 | 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 |
|---|---|---|
| 859.4 | 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 |
|---|---|---|---|
| 6.960 ± 0.001 | LS | Shchuka, Motyka, et al., 1989 | LL |
| 6.90 ± 0.01 | PE | Dewar and Goodman, 1972 | LLK |
| 7.00 ± 0.01 | PE | Boschi, Murrell, et al., 1972 | LLK |
| 7.1 ± 0.1 | EI | Gallegos, 1968 | RDSH |
| 7.10 | CTS | Kuroda, 1964 | RDSH |
| 6.85 | CTS | Finch, 1964 | RDSH |
| 7.11 | CTS | Briegleb, 1964 | RDSH |
| 7.06 | CTS | Kinoshita, 1962 | RDSH |
| 7.1 | CTS | Briegleb, Czekalla, et al., 1961 | RDSH |
| 7.03 | CTS | Birks and Stifkin, 1961 | RDSH |
| 7.15 | CTS | Briegleb and Czekalla, 1959 | RDSH |
| 6.83 | CTS | Matsen, 1956 | RDSH |
| 6.97 | PE | Clar and Schmidt, 1977 | Vertical value; LLK |
| 6.97 | PE | Clar and Schmidt, 1976 | Vertical value; LLK |
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.
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]
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]
Pongratz and Griengl, 1929
Pongratz, A.; Griengl, F.,
Uber Verbrennungswarmen des Perylens und einiger seiner Derivate (XXVI. MitteHung) Untersuchungen uber Perylen und seine Derivate,
Monatsh. Chem., 1929, 53, 256-262. [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]
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]
Scheidt and Weinkauf, 1997
Scheidt, J.; Weinkauf, R.,
Photodetachment photoelectron spectroscopy of Perylene and CS2: Two Extreme Cases.,
Chem. Phys. Lett., 1997, 274, 1-3, 18, https://doi.org/10.1016/S0009-2614(97)00648-9
. [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]
Chen and Cooks, 1995
Chen, G.D.; Cooks, R.G.,
Electron affinities of polycyclic aromatic hydrocarbons determined by the kinetic method,
J. Mass Spectrom., 1995, 30, 8, 1167, https://doi.org/10.1002/jms.1190300814
. [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]
Shchuka, Motyka, et al., 1989
Shchuka, M.I.; Motyka, A.L.; Topp, M.R.,
Two-photon threshold ionization spectroscopy of perylene and Van der Waals complexes,
Chem. Phys. Lett., 1989, 164, 87. [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]
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]
Gallegos, 1968
Gallegos, E.J.,
Mass spectrometry and ionization energies of some condensed-ring aromatic and heterocyclic compounds,
J. Phys. Chem., 1968, 72, 3452. [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]
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]
Clar and Schmidt, 1977
Clar, E.; Schmidt, W.,
Correlations between photoelectron and ultraviolet absorption spectra of polycyclic hydrocarbons. The perylene, coronene and bisanthene series,
Tetrahedron, 1977, 33, 2093. [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]
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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