Pyrene

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Gas phase thermochemistry data

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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
Δfgas225.5 ± 2.5kJ/molReviewRoux, Temprado, et al., 2008There are sufficient literature values to make a qualified recommendation where the suggested value is in good agreement with values predicted using thermochemical cycles or from reliable estimates. In general, the evaluated uncertainty limits are on the order of (2 to 4) kJ/mol.; DRB
Δfgas225.7 ± 1.3kJ/molCcrSmith, Stewart, et al., 1980ALS
Δfgas214.9kJ/molN/AWestrum and Wong, 1967Value computed using ΔfHsolid° value of 114.7±0.4 kj/mol from Westrum and Wong, 1967 and ΔsubH° value of 100.2 kj/mol from Smith, Stewart, et al., 1980.; DRB
Δfgas214.9kJ/molN/ARichardson and Parks, 1939Value computed using ΔfHsolid° value of 114.7±3.6 kj/mol from Richardson and Parks, 1939 and ΔsubH° value of 100.2 kj/mol from Smith, Stewart, et al., 1980.; DRB

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
40.3050.Dorofeeva O.V., 1988These functions are also reproduced in the reference book [ Frenkel M., 1994]. Recommended entropy and heat capacity values are in close agreement with other statistically calculated values [ Smith N.K., 1980] at T=400-500 K. The disagreement increases up to 2 J/mol*K for T=200 and 600 K.; GT
62.82100.
94.01150.
129.90200.
185.37273.15
204.2 ± 1.0298.15
205.58300.
275.54400.
333.59500.
379.87600.
416.74700.
446.49800.
470.86900.
491.071000.
507.981100.
522.251200.
534.371300.
544.731400.
553.621500.

Condensed phase thermochemistry data

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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
Δfsolid125.2 ± 2.3kJ/molReviewRoux, Temprado, et al., 2008There are sufficient literature values to make a qualified recommendation where the suggested value is in good agreement with values predicted using thermochemical cycles or from reliable estimates. In general, the evaluated uncertainty limits are on the order of (2 to 4) kJ/mol.; DRB
Δfsolid125.5 ± 1.2kJ/molCcrSmith, Stewart, et al., 1980ALS
Δfsolid114.7 ± 0.4kJ/molCcrWestrum and Wong, 1967ALS
Δfsolid114.7 ± 3.6kJ/molCcbRichardson and Parks, 1939Reanalyzed by Cox and Pilcher, 1970, Original value = 112.5 kJ/mol; see Richardson, 1939; ALS
Quantity Value Units Method Reference Comment
Δcsolid-7850.7 ± 1.0kJ/molCcrSmith, Stewart, et al., 1980Corresponding Δfsolid = 125.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-7840.1 ± 0.4kJ/molCcrWestrum and Wong, 1967Corresponding Δfsolid = 114.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-7840.0 ± 3.5kJ/molCcbRichardson and Parks, 1939Reanalyzed by Cox and Pilcher, 1970, Original value = -7836.51 kJ/mol; see Richardson, 1939; Corresponding Δfsolid = 114.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar224.89J/mol*KN/AWong and Westrum, 1971DH
solid,1 bar215.1J/mol*KN/AJacobs and Parks, 1934Extrapolation below 90 K, 59.79 J/mol*K. Hump in Cp curve around 116 K, probably 2nd order transition. H = 100 J/mol.; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
229.36298.15Smith, Stewart, et al., 1980DH
229.70298.15Wong and Westrum, 1971T = 5 to 484 K.; DH
227.65291.1Jacobs and Parks, 1934T = 94 to 292 K. Value is unsmoothed experimental datum.; DH

Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C16H10+ + Pyrene = (C16H10+ • Pyrene)

By formula: C16H10+ + C16H10 = (C16H10+ • C16H10)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr79.9kJ/molPHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Δr120.J/mol*KN/AMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
34.390.PHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated

C16H11+ + Pyrene = (C16H11+ • Pyrene)

By formula: C16H11+ + C16H10 = (C16H11+ • C16H10)

Quantity Value Units Method Reference Comment
Δr69.0kJ/molPHPMSMeot-Ner (Mautner), 1980gas phase
Quantity Value Units Method Reference Comment
Δr120.J/mol*KPHPMSMeot-Ner (Mautner), 1980gas phase

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction 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

View reactions leading to C16H10+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)7.426 ± 0.001eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)869.2kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity840.1kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.406 ± 0.010LPESAndo, Kokubo, et al., 2004B
0.39002ECDWentworth and Becker, 1962B
0.500 ± 0.030ECDLyons, Morris, et al., 1968B
0.5910 ± 0.0080ECDBecker and Chen, 1966B

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
867.8Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
841.8Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Ionization energy determinations

IE (eV) Method Reference Comment
7.4256 ± 0.0006LSHager and Wallace, 1988LL
7.4PEClar, Robertson, et al., 1981LLK
7.50 ± 0.05EQMautner(Meot-Ner), 1980LLK
7.41PEClar and Schmidt, 1979LLK
7.45 ± 0.01PEDewar and Goodman, 1972LLK
7.7 ± 0.3EIWacks, 1964RDSH
7.70CTSKuroda, 1964RDSH
7.31CTSFinch, 1964RDSH
7.72CTSBriegleb, 1964RDSH
7.48CTSKinoshita, 1962RDSH
7.45CTSBriegleb, Czekalla, et al., 1961RDSH
7.55CTSBirks and Stifkin, 1961RDSH
7.53CTSBriegleb and Czekalla, 1959RDSH
7.58CTSMatsen, 1956RDSH
7.42PEAkiyama, Li, et al., 1979Vertical value; LLK
7.41PEClar and Schmidt, 1976Vertical value; LLK
7.41PEBoschi and Schmidt, 1972Vertical value; LLK

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction 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]

Smith, Stewart, et al., 1980
Smith, N.K.; Stewart, R.C., Jr.; Osborn, A.G.; Scott, D.W., Pyrene: vapor pressure, enthalpy of combustion, and chemical thermodynamic properties, J. Chem. Thermodyn., 1980, 12, 919-926. [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]

Richardson and Parks, 1939
Richardson, J.W.; Parks, G.S., Thermal data on organic compounds. XIX. Modern combustion data for some non-volatile compounds containing carbon, hydrogen and oxygen, J. Am. Chem. Soc., 1939, 61, 3543-3546. [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]

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]

Smith N.K., 1980
Smith N.K., Jr., Pyrene: vapor pressure, enthalpy of combustion, and chemical thermodynamic properties, J. Chem. Thermodyn., 1980, 12, 919-926. [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]

Richardson, 1939
Richardson, J.W., Precise determination of the heats of combustion of some representative organic compounds, Ph.D. Thesis for Standford University, 1939, 1-122. [all data]

Wong and Westrum, 1971
Wong, W-K.; Westrum, E.F., Jr., Thermodynamics of polynuclear aromatic molecules. I. Heat capacities and enthalpies of fusion of pyrene, flouranthene, and triphenylene, J. Chem. Thermodynam., 1971, 3, 105-124. [all data]

Jacobs and Parks, 1934
Jacobs, C.J.; Parks, G.S., Thermal data on organic compounds. XIV. Some heat capacity, entropy and free energy data for cyclic substances, J. Am. Chem. Soc., 1934, 56, 1513-1517. [all data]

Meot-Ner (Mautner), 1980
Meot-Ner (Mautner), M., Dimer Cations of Polycyclic Aromatics: Experimental Bonding Energies and Resonance Stabilization, J. Phys. Chem., 1980, 84, 21, 2724, https://doi.org/10.1021/j100458a012 . [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, Kokubo, et al., 2004
Ando, N.; Kokubo, S.; Mitsui, M.; Nakajima, A., Photoelectron spectroscopy of pyrene cluster anions, (pyrene)(-)(n) (n=1-20), Chem. Phys. Lett., 2004, 389, 4-6, 279-283, https://doi.org/10.1016/j.cplett.2004.03.100 . [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]

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]

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]

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]

Clar, Robertson, et al., 1981
Clar, E.; Robertson, J.M.; Schlogl, R.; Schmidt, W., Photoelectron spectra of polynuclear aromatics. 6. Application to structural elucidation: 'Circumanthracene', J. Am. Chem. Soc., 1981, 103, 1320. [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]

Clar and Schmidt, 1979
Clar, E.; Schmidt, W., Correlations between photoelectron and UV absorption spectra of polycyclic hydrocarbons. The pyrene series, Tetrahedron, 1979, 35, 1027. [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]

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]

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]

Akiyama, Li, et al., 1979
Akiyama, I.; Li, K.C.; LeBreton, P.R.; Fu, P.P.; Harvey, R.G., Ultraviolet photoelectron studies of polycyclic aromatic hydrocarbons. The ground-state electronic structure of aryloxiranes and metabolites of benzo[a]pyrene, J. Phys. Chem., 1979, 83, 2997. [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]

Boschi and Schmidt, 1972
Boschi, R.; Schmidt, W., Photoelectron spectra of polycyclic aromatic hydrocarbons. Pyrene and coronene, Tetrahedron Lett., 1972, 25, 2577. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References