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, 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 | -44.65 ± 0.17 | kcal/mol | Ccb | Pilcher and Sutton, 1956 | ALS |
ΔfH°solid | -44.10 ± 0.15 | kcal/mol | Ccb | Parks, Manchester, et al., 1954 | ALS |
ΔfH°solid | -44.09 | kcal/mol | Ccb | Schreiner, 1925 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -651.482 | kcal/mol | Ccb | Magnus, 1956 | Corresponding ΔfHºsolid = -49.455 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -656.29 ± 0.10 | kcal/mol | Ccb | Pilcher and Sutton, 1956 | Corresponding ΔfHºsolid = -44.65 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -656.84 | kcal/mol | Ccb | Parks, Manchester, et al., 1954 | Corresponding ΔfHºsolid = -44.10 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -656.85 | kcal/mol | Ccb | Schreiner, 1925 | Corresponding ΔfHºsolid = -44.09 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -658.0 | kcal/mol | Ccb | Swietoslawski and Starczedska, 1925 | Corresponding ΔfHºsolid = -42.9 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
30.21 | 298.15 | Ueberreiter and Orthmann, 1950 | T = 293 to 368 K. Equation only.; DH |
31.60 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 160°C.; DH |
31.00 | 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, 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° | 15.9 ± 0.38 | kcal/mol | DSC | Rojas-Aguilar, Flores-Lara, et al., 2004 | AC |
ΔsubH° | 15.0 | kcal/mol | C | Magnus, 1956 | ALS |
ΔsubH° | 15.000 | kcal/mol | V | Coolidge and Coolidge, 1927 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.4 | 395. | A | Stephenson and Malanowski, 1987 | Based on data from 388. to 402. K.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
16.3 ± 0.1 | 262. | ME,TE | de Kruif, 1981 | AC |
15.0 | 269. | QF | Coolidge and Coolidge, 1927 | Based on data from 260. to 278. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
4.40 ± 0.02 | 385.1 | DSC | Rojas-Aguilar, Flores-Lara, et al., 2004 | AC |
4.39 ± 0.07 | 385.7 | HFC | Rojas-Aguilar, Flores-Lara, et al., 2004 | AC |
4.410 | 388. | N/A | Acree, 1991 | AC |
4.4097 | 386.0 | N/A | Andrews, Lynn, et al., 1926 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.4 | 386.0 | Andrews, Lynn, et al., 1926 | DH |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid 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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