p-Benzoquinone
- Formula: C6H4O2
- Molecular weight: 108.0948
- IUPAC Standard InChIKey: AZQWKYJCGOJGHM-UHFFFAOYSA-N
- CAS Registry Number: 106-51-4
- 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: 2,5-Cyclohexadiene-1,4-dione; p-Quinone; Chinone; Quinone; 1,4-Benzoquinone; 1,4-Cyclohexadienedione; Benzoquinone; Benzo-chinon; Chinon; Cyclohexadienedione; NCI-C55845; 1,4-Benzoquine; 1,4-Cyclohexadiene dioxide; 1,4-Diossibenzene; 1,4-Dioxy-benzol; p-Chinon; Rcra waste number U197; UN 2587; USAF P-220; Steara PBQ; NSC 36324
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Condensed phase thermochemistry data
Go To: Top, Phase change 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 as indicated in comments:
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 | -186.8 ± 0.71 | kJ/mol | Ccb | Pilcher and Sutton, 1956 | ALS |
ΔfH°solid | -184.5 ± 0.63 | kJ/mol | Ccb | Parks, Manchester, et al., 1954 | ALS |
ΔfH°solid | -184.5 | kJ/mol | Ccb | Schreiner, 1925 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -2725.80 | kJ/mol | Ccb | Magnus, 1956 | Corresponding ΔfHºsolid = -206.92 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -2745.9 ± 0.42 | kJ/mol | Ccb | Pilcher and Sutton, 1956 | Corresponding ΔfHºsolid = -186.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -2748.2 | kJ/mol | Ccb | Parks, Manchester, et al., 1954 | Corresponding ΔfHºsolid = -184.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -2748.3 | kJ/mol | Ccb | Schreiner, 1925 | Corresponding ΔfHºsolid = -184.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -2753. | kJ/mol | Ccb | Swietoslawski and Starczedska, 1925 | Corresponding ΔfHºsolid = -179. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
126.4 | 298.15 | Ueberreiter and Orthmann, 1950 | T = 293 to 368 K. Equation only.; DH |
132.2 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 160°C.; DH |
129.7 | 291.2 | Lange, 1924 | T = 22 to 291 K. Value is unsmoothed experimental datum.; DH |
Phase change data
Go To: Top, Condensed phase 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
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 |
---|---|---|---|---|---|
Tfus | 386.0 | K | N/A | Andrews, Lynn, et al., 1926, 2 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 66.7 ± 1.6 | kJ/mol | DSC | Rojas-Aguilar, Flores-Lara, et al., 2004 | AC |
ΔsubH° | 62.8 | kJ/mol | C | Magnus, 1956 | ALS |
ΔsubH° | 62.760 | kJ/mol | V | Coolidge and Coolidge, 1927 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
47.8 | 395. | A | Stephenson and Malanowski, 1987 | Based on data from 388. to 402. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
68.0 ± 0.5 | 262. | ME,TE | de Kruif, 1981 | AC |
62.8 | 269. | QF | Coolidge and Coolidge, 1927 | Based on data from 260. to 278. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
18.4 ± 0.1 | 385.1 | DSC | Rojas-Aguilar, Flores-Lara, et al., 2004 | AC |
18.4 ± 0.3 | 385.7 | HFC | Rojas-Aguilar, Flores-Lara, et al., 2004 | AC |
18.45 | 388. | N/A | Acree, 1991 | AC |
18.450 | 386.0 | N/A | Andrews, Lynn, et al., 1926 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
47.8 | 386.0 | Andrews, Lynn, et al., 1926 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change 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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 10.0 ± 0.1 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 799.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 769.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.850 ± 0.010 | LPES | Fu, Yang, et al., 2011 | Triplet state of neutral 2.32 eV up; B |
1.8600 ± 0.0050 | LPES | Schiedt and Weinkauf, 1999 | Neutral T1 state is 2.3 eV up: Siegert, Vogeler, et al., 20112; B |
1.91 ± 0.10 | TDEq | Heinis, Chowdhury, et al., 1988 | ΔGea(423 K) = -42.4 kcal/mol; ΔSea = -4.0 eu.; B |
1.930 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -43.1 kcal/mol; ΔSea =-4.0, est. from data in Heinis, Chowdhury, et al., 1988; B |
1.990 ± 0.048 | LPD | Marks, Comita, et al., 1985 | B |
1.89 ± 0.30 | NBIE | Cooper, Naff, et al., 1975 | B |
1.370 ± 0.078 | SI | Farragher and Page, 1966 | The Magnetron method, lacking mass analysis, is not considered reliable.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.11 | PE | Lauer, Schafer, et al., 1975 | LLK |
10.01 | PE | Kobayashi, 1975 | LLK |
9.96 ± 0.01 | PI | Kotov and Potapov, 1972 | LLK |
9.96 ± 0.01 | PI | Potapov and Sorokin, 1971 | LLK |
9.95 | PE | Dewar and Worley, 1969 | RDSH |
9.7 | PI | Terenin, 1961 | RDSH |
9.67 ± 0.02 | PI | Vilesov and Terenin, 1957 | RDSH |
10.1 | PE | Bock, Mohmand, et al., 1983 | Vertical value; LBLHLM |
9.99 ± 0.05 | PE | Dougherty and McGlynn, 1977 | Vertical value; LLK |
10.03 | PE | Cowan, Gleiter, et al., 1971 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C4H2O2+ | 11.2 ± 0.05 | C2H2 | PI | Potapov and Sorokin, 1971 | LLK |
C5H4O+ | 11.10 ± 0.05 | CO | PI | Potapov and Sorokin, 1971 | LLK |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change 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
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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-1277 |
NIST MS number | 227766 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change 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.
Pilcher and Sutton, 1956
Pilcher, G.; Sutton, L.E.,
The heats of combustion of quinol and p-benzoquinone and the thermodynamic quantities of the oxidation-reduction reaction,
J. Chem. Soc., 1956, 2695-2700. [all data]
Parks, Manchester, et al., 1954
Parks, G.S.; Manchester, K.E.; Vaughan, L.M.,
Heats of combustion and formation of some alcohols, phenols, and ketones,
J. Chem. Phys., 1954, 22, 2089-2090. [all data]
Schreiner, 1925
Schreiner, E.,
Thermodynamics of the quinhydrone electrode and the chemical constant of hydrogen,
Z. Phys. Chem., 1925, 117, 57-87. [all data]
Magnus, 1956
Magnus, A.,
Die resonanzenergien der parachinone Aui grund der prazisionsmessungsen ihrer verbrennungswarmen durch herrn gerhard wittwer,
Z. Phys. Chem. (Neue Folge), 1956, 9, 141-161. [all data]
Swietoslawski and Starczedska, 1925
Swietoslawski, W.; Starczedska, H.,
Correction des donnees thermochimiques de M.A. Valeur,
J. Chem. Phys., 1925, 22, 399-401. [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]
Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J.,
The heat capacities and heat of crystallization of some isomeric aromatic compounds,
J. Am. Chem. Soc., 1926, 48, 1274-1287. [all data]
Lange, 1924
Lange, F.,
Untersuchungen über die spezifische Wärme bei tiefen Temperaturen,
Z. Phys. Chem., 1924, 110, 343-362. [all data]
Andrews, Lynn, et al., 1926, 2
Andrews, D.H.; Lynn, G.; Johnston, J.,
The Heat Capacities and Heat of Crystallization of Some Isomeric Aromatic Compounds,
J. Am. Chem. Soc., 1926, 48, 1274. [all data]
Rojas-Aguilar, Flores-Lara, et al., 2004
Rojas-Aguilar, Aarón; Flores-Lara, Honorio; Martinez-Herrera, Melchor; Ginez-Carbajal, Francisco,
Thermochemistry of benzoquinones,
The Journal of Chemical Thermodynamics, 2004, 36, 6, 453-463, https://doi.org/10.1016/j.jct.2004.03.002
. [all data]
Coolidge and Coolidge, 1927
Coolidge, A.S.; Coolidge, M.S.,
The sublimation pressures of substituted quinones and hydroquinones,
J. Am. Chem. Soc., 1927, 49, 100-104. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
de Kruif, 1981
de Kruif, C.G.,
Thermodynamic properties of 1,4-benzoquinone (BQ), 1,4-hydroquinone (HQ), 1,4-naphthoquinone (NQ), 1,4-naphthohydroquinone (NHQ), and the complexes BQ--HQ 1:1, NQ--HQ 1:1, NQ--NHQ 2:1, and NQ--NHQ 1:1,
J. Chem. Phys., 1981, 74, 10, 5838, https://doi.org/10.1063/1.440898
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [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]
Fu, Yang, et al., 2011
Fu, Q.A.; Yang, J.L.; Wang, X.B.,
On the Electronic Structures and Electron Affinities of the m-Benzoquinone (BQ) Diradical and the o-, p-BQ Molecules: A Synergetic Photoelectron Spectroscopic and Theoretical Study,
J. Phys. Chem. A, 2011, 115, 15, 3201-3207, https://doi.org/10.1021/jp1120542
. [all data]
Schiedt and Weinkauf, 1999
Schiedt, J.; Weinkauf, R.,
Resonant Photodetachment via Shape and Feshbach Resonances: p-Benzoquinone Anions as a Model System,
J. Chem. Phys., 1999, 110, 1, 304, https://doi.org/10.1063/1.478066
. [all data]
Siegert, Vogeler, et al., 2011
Siegert, S.; Vogeler, F.; Marian, C.M.; Weinkauf, R.,
Throwing light on dark states of alpha-oligothiophenes of chain lengths 2 to 6: radical anion photoelectron spectroscopy and excited-state theory,
Phys. Chem. Chem. Phys., 2011, 13, 21, 10350-10363, https://doi.org/10.1039/c0cp02712j
. [all data]
Heinis, Chowdhury, et al., 1988
Heinis, T.; Chowdhury, S.; Scott, S.L.; Kebarle, P.,
Electron Affinities of Benzo-, Naphtho-, and Anthraquinones Determined from Gas-Phase Equilibria Measurements,
J. Am. Chem. Soc., 1988, 110, 2, 400, https://doi.org/10.1021/ja00210a015
. [all data]
Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr.,
Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO2) from 74CEL/BEN],
J. Am. Chem. Soc., 1985, 107, 2291. [all data]
Marks, Comita, et al., 1985
Marks, J.; Comita, P.B.; Brauman, J.I.,
Threshold resonances in electron photodetachment spectra. Structural evidence for dipole-supported states,
J. Am. Chem. Soc., 1985, 107, 3718. [all data]
Cooper, Naff, et al., 1975
Cooper, C.D.; Naff, W.T.; Compton, R.N.,
Negative ion properties of p-benzoquinone: Electron affinity and compound states,
J. Chem. Phys., 1975, 63, 2752. [all data]
Farragher and Page, 1966
Farragher, A.L.; Page, F.M.,
Experimental Determination of Electron Affinities. Part 9. - Benzoquinone, Chloranil and Related Compounds,
Trans. Farad. Soc., 1966, 62, 3072, https://doi.org/10.1039/tf9666203072
. [all data]
Lauer, Schafer, et al., 1975
Lauer, G.; Schafer, W.; Schweig, A.,
Assignment of the four lowest ionized states of p-benzoquinone and the question of "lone pair" splitting in this system,
Chem. Phys. Lett., 1975, 33, 312. [all data]
Kobayashi, 1975
Kobayashi, T.,
Photoelectron spectra of p-benzoquinones,
J. Electron. Spectrosc. Relat. Phenom., 1975, 7, 349. [all data]
Kotov and Potapov, 1972
Kotov, B.V.; Potapov, V.K.,
Ionization potentials of strong organic electron acceptors,
Khim. Vys. Energ., 1972, 6, 375. [all data]
Potapov and Sorokin, 1971
Potapov, V.K.; Sorokin, V.V.,
Photoionization and ion-molecule reactions in quinones and alcohols,
High Energy Chem., 1971, 5, 435, In original 487. [all data]
Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation,
J. Chem. Phys., 1969, 50, 654. [all data]
Terenin, 1961
Terenin, A.,
Charge transfer in organic solids, induced by light,
Proc. Chem. Soc., London, 1961, 321. [all data]
Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N.,
The photoionization of the vapors of certain organic compounds,
Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]
Bock, Mohmand, et al., 1983
Bock, H.; Mohmand, S.; Hirabayashi, T.; Maier, G.; Reisenauer, H.P.,
Photoelektronen-spektroskopischer nachweis und matrix-isolierung von thio-para-benzochinonen,
Chem. Ber., 1983, 116, 273. [all data]
Dougherty and McGlynn, 1977
Dougherty, D.; McGlynn, S.P.,
Photoelectron spectroscopy of carbonyls. 1,4-Benzoquinones,
J. Am. Chem. Soc., 1977, 99, 3234. [all data]
Cowan, Gleiter, et al., 1971
Cowan, D.O.; Gleiter, R.; Hashmall, J.A.; Heilbronner, E.; Hornung, V.,
Interaction between the orbitals of lone pair electrons in dicarbonyl compounds,
Angew. Chem. Int. Ed. Engl., 1971, 10, 401. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,solid Constant pressure heat capacity of solid EA Electron affinity IE (evaluated) Recommended ionization energy Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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