Pyrene
- Formula: C16H10
- Molecular weight: 202.2506
- IUPAC Standard InChIKey: BBEAQIROQSPTKN-UHFFFAOYSA-N
- CAS Registry Number: 129-00-0
- 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: β-Pyrene; Benzo[def]phenanthrene; Pyren; Coal tar pitch volatiles:pyrene
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Reaction thermochemistry data
Go To: Top, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
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
By formula: C16H10+ + C16H10 = (C16H10+ • C16H10)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 79.9 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 120. | J/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
34. | 390. | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated |
By formula: C16H11+ + C16H10 = (C16H11+ • C16H10)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 69.0 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 120. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1980 | gas phase |
Henry's Law data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference |
---|---|---|---|
84. | L | N/A | |
92. | M | N/A |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, Henry's Law data, Mass spectrum (electron ionization), 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 ± 0.001 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 869.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 840.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.406 ± 0.010 | LPES | Ando, Kokubo, et al., 2004 | B |
0.39002 | ECD | Wentworth and Becker, 1962 | B |
0.500 ± 0.030 | ECD | Lyons, Morris, et al., 1968 | B |
0.5910 ± 0.0080 | ECD | Becker and Chen, 1966 | B |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
867.8 | 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 |
---|---|---|
841.8 | 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 |
---|---|---|---|
7.4256 ± 0.0006 | LS | Hager and Wallace, 1988 | LL |
7.4 | PE | Clar, Robertson, et al., 1981 | LLK |
7.50 ± 0.05 | EQ | Mautner(Meot-Ner), 1980 | LLK |
7.41 | PE | Clar and Schmidt, 1979 | LLK |
7.45 ± 0.01 | PE | Dewar and Goodman, 1972 | LLK |
7.7 ± 0.3 | EI | Wacks, 1964 | RDSH |
7.70 | CTS | Kuroda, 1964 | RDSH |
7.31 | CTS | Finch, 1964 | RDSH |
7.72 | CTS | Briegleb, 1964 | RDSH |
7.48 | CTS | Kinoshita, 1962 | RDSH |
7.45 | CTS | Briegleb, Czekalla, et al., 1961 | RDSH |
7.55 | CTS | Birks and Stifkin, 1961 | RDSH |
7.53 | CTS | Briegleb and Czekalla, 1959 | RDSH |
7.58 | CTS | Matsen, 1956 | RDSH |
7.42 | PE | Akiyama, Li, et al., 1979 | Vertical value; LLK |
7.41 | PE | Clar and Schmidt, 1976 | Vertical value; LLK |
7.41 | PE | Boschi and Schmidt, 1972 | Vertical value; LLK |
Mass spectrum (electron ionization)
Go To: Top, Reaction thermochemistry data, Henry's Law 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW- 129 |
NIST MS number | 227992 |
References
Go To: Top, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
EA Electron affinity IE (evaluated) Recommended ionization energy T Temperature d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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