1,2-Benzenediol
- Formula: C6H6O2
- Molecular weight: 110.1106
- IUPAC Standard InChIKey: YCIMNLLNPGFGHC-UHFFFAOYSA-N
- CAS Registry Number: 120-80-9
- 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: Pyrocatechol; o-Benzenediol; o-Dihydroxybenzene; o-Dioxybenzene; o-Hydroxyphenol; o-Phenylenediol; c.i. Oxidation base 26; c.i. 76500; Catechol; Catechol (phenol); Durafur developer c; Fouramine pch; Fourrine 68; Oxyphenic acid; Pelagol grey c; Phthalhydroquinone; Pyrocatechin; Pyrocatechine; 1,2-Dihydroxybenzene; 2-Hydroxyphenol; o-Hydroquinone; Benzene, o-dihydroxy-; NCI-C55856; o-Diphenol; Katechol; Pyrokatechin; Pyrokatechol; Kachin; 2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-,(2R-trans)-; NSC 1573; 1,2-Benzenediol (pyrocatechol); o-catecol
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -274.8 ± 1.2 | kJ/mol | Ccr | Sabbah and Buluku, 1991 | ΔHfusion =15.00±0.34 kJ/mol; ALS |
ΔfH°gas | -267.5 ± 1.9 | kJ/mol | Ccb | Ribeiro Da Silva and Ribeiro Da Silva, 1984 | ALS |
ΔfH°gas | -271.6 ± 2.0 | kJ/mol | Ccb | Finch, Gardner, et al., 1983 | ALS |
ΔfH°gas | -262.5 | kJ/mol | N/A | Pushin, 1954 | Value computed using ΔfHsolid° value of -344.0 kj/mol from Pushin, 1954 and ΔsubH° value of 81.5 kj/mol from Sabbah and Buluku, 1991.; DRB |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
34.39 | 50. | Kudchadker S.A., 1979 | GT |
45.32 | 100. | ||
62.77 | 150. | ||
82.10 | 200. | ||
110.62 | 273.15 | ||
120.09 | 298.15 | ||
120.78 | 300. | ||
155.47 | 400. | ||
183.90 | 500. | ||
206.30 | 600. | ||
223.91 | 700. | ||
237.92 | 800. | ||
249.27 | 900. | ||
258.60 | 1000. | ||
266.38 | 1100. | ||
272.93 | 1200. | ||
278.49 | 1300. | ||
283.25 | 1400. | ||
287.35 | 1500. |
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:
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 | -362.3 ± 1.1 | kJ/mol | Ccr | Sabbah and Buluku, 1991 | ΔHfusion =15.00±0.34 kJ/mol; ALS |
ΔfH°solid | -354.1 ± 1.1 | kJ/mol | Ccb | Ribeiro Da Silva and Ribeiro Da Silva, 1984 | ALS |
ΔfH°solid | -353.1 ± 1.1 | kJ/mol | Ccb | Finch, Gardner, et al., 1983 | ALS |
ΔfH°solid | -344. | kJ/mol | Ccb | Pushin, 1954 | Author's hf298_condensed=-83.8 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -2856.3 ± 1.1 | kJ/mol | Ccr | Sabbah and Buluku, 1991 | ΔHfusion =15.00±0.34 kJ/mol; Corresponding ΔfHºsolid = -362.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -2864.5 ± 0.8 | kJ/mol | Ccb | Ribeiro Da Silva and Ribeiro Da Silva, 1984 | Corresponding ΔfHºsolid = -354.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -2865.49 ± 0.74 | kJ/mol | Ccb | Finch, Gardner, et al., 1983 | Corresponding ΔfHºsolid = -353.06 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -2874. | kJ/mol | Ccb | Pushin, 1954 | Author's hf298_condensed=-83.8 kcal/mol; Corresponding ΔfHºsolid = -344. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -2862. | kJ/mol | Ccb | Barker, 1925 | Author was aware that data differs from previously reported values; Corresponding ΔfHºsolid = -357. 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 |
---|---|---|---|
140.17 | 298.15 | Bret-Dibat and Lichanot, 1989 | T = 200 to 500 K. Cp(c) = 132.494 + 0.2808t + 5.4046x10-4t2 + 2.0581x10-5t3 J/mol*K (t/°C). Cp value calculated from equation.; DH |
140.6 | 298.15 | Ueberreiter and Orthmann, 1950 | T = 293 to 368 K. Equation only.; DH |
156.9 | 323. | Satoh and Sogabe, 1941 | T = 0 to 100°C. Mean value.; DH |
132.2 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 200°C.; DH |
139.3 | 297.9 | Andrews, 1926 | T = 110 to 344 K. Value is unsmoothed experimental datum.; DH |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
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
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 518.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 513. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tboil | 518.8 | K | N/A | Krupatkin and Rozhentsova, 1971 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tboil | 519.05 | K | N/A | Lecat, 1943 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 377. ± 1. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 377.5 | K | N/A | Andrews, Lynn, et al., 1926, 2 | Uncertainty assigned by TRC = 0.2 K; obtained from cooling curve in absence of air; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 71.9 ± 0.8 | kJ/mol | GS | Verevkin and Kozlova, 2008 | Based on data from 378. to 389. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 86. ± 4. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
63.1 | 410. | A | Stephenson and Malanowski, 1987 | Based on data from 395. to 519. K.; AC |
61.2 | 393. | GC | Kundel, Lille, et al., 1975 | Based on data from 378. to 439. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
391.7 to 518.7 | 5.5033 | 2713.153 | -23.96 | von Terres, Gebert, et al., 1955 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
80.0 ± 0.5 | 302. | N/A | Chen, Oja, et al., 2006 | Based on data from 295. to 310. K.; AC |
81. ± 2. | 309. | V | Wolf and Weghofer, 1938 | ALS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
22.000 | 376.85 | N/A | Bret-Dibat and Lichanot, 1989 | DH |
22.87 | 377.6 | N/A | Verevkin and Kozlova, 2008 | AC |
18.55 | 377.6 | N/A | Verevkin and Schick, 2000 | AC |
22.54 | 377.7 | DSC | Lee, Chang, et al., 1997 | AC |
22.01 | 376.9 | N/A | Bret-Dibat and Lichanot, 1989 | AC |
22.760 | 337.5 | N/A | Andrews, Lynn, et al., 1926 | DH |
22.76 | 377.5 | C | Andrews, Lynn, et al., 1926 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
58. | 376.85 | Bret-Dibat and Lichanot, 1989 | DH |
60.3 | 337.5 | Andrews, Lynn, et al., 1926 | DH |
Henry's Law 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: 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 |
---|---|---|---|
4600. | V | N/A |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law 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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C6H6O2+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.15 | PE | Palmer, Moyes, et al., 1979 | LLK |
8.56 | PE | Palmer, Moyes, et al., 1979 | Vertical value; LLK |
De-protonation reactions
C6H5O2- + =
By formula: C6H5O2- + H+ = C6H6O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1420. ± 8.8 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1422. ± 11. | kJ/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1392. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 1393. ± 8.4 | kJ/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law 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.
Sabbah and Buluku, 1991
Sabbah, R.; Buluku, E.N.L.E.,
Thermodynamic study of three isomers of dihydroxybenzene,
Can. J. Chem., 1991, 69, 481-488. [all data]
Ribeiro Da Silva and Ribeiro Da Silva, 1984
Ribeiro Da Silva, M.D.M.C.; Ribeiro Da Silva, M.A.V.,
Enthalpies of combustion of 1,2-dihydroxybenzene and of six alkylsubstituted 1,2-dihydroxybenzenes,
J. Chem. Thermodyn., 1984, 16, 1149-1155. [all data]
Finch, Gardner, et al., 1983
Finch, A.; Gardner, P.J.; Wu, D.,
Studies on nitrophenols. Part IV. The standard enthalpies of combustion and formation of 1,2-dihydroxybenzene, 1,2- and 1,4-nitrophenol,
Thermochim. Acta, 1983, 66, 333-342. [all data]
Pushin, 1954
Pushin, N.A.,
Heats of combustion and heats of formation of isomeric organic compounds,
Bull. Soc. Chim. Belgrade, 1954, 19, 531-547. [all data]
Kudchadker S.A., 1979
Kudchadker S.A.,
Ideal gas thermodynamic properties of benzene diols: pyrocatechol, resorcinol, and hydroquinone,
Thermochim. Acta, 1979, 30, 319-326. [all data]
Barker, 1925
Barker, M.F.,
Calorific value and constitution,
J. Phys. Chem., 1925, 29, 1345-1363. [all data]
Bret-Dibat and Lichanot, 1989
Bret-Dibat, P.; Lichanot, A.,
Thermodynamic properties of positional isomers of disubstituted benzene in condensed phase,
Thermochim. Acta, 1989, 147(2), 261-271. [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]
Satoh and Sogabe, 1941
Satoh, S.; Sogabe, T.,
The heat capacities of some organic compounds containing nitrogen and the atomic heat of nitrogen. (3), Sci.,
Pap. Inst. Phys. Chem. Res. (Tokyo), 1941, 38, 238-245. [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]
Andrews, 1926
Andrews, D.H.,
The specific heats of some isomers of the type ortho, meta and para C6H4XY from 110 to 340K,
J. Am. Chem. Soc., 1926, 48, 1287-1298. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]
Krupatkin and Rozhentsova, 1971
Krupatkin, I.L.; Rozhentsova, E.P.,
Some properties of systems with latent liquid immiscibility,
Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 1700. [all data]
Lecat, 1943
Lecat, M.,
Azeotropes of Ethyl Urethane and other Azeotropes,
C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [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]
Verevkin and Kozlova, 2008
Verevkin, Sergey P.; Kozlova, Svetlana A.,
Di-hydroxybenzenes: Catechol, resorcinol, and hydroquinone,
Thermochimica Acta, 2008, 471, 1-2, 33-42, https://doi.org/10.1016/j.tca.2008.02.016
. [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]
Kundel, Lille, et al., 1975
Kundel, H.; Lille, U.; Kaidas, N.,
Tr. Tallin. Politekh. Inst., 1975, 390, 107. [all data]
von Terres, Gebert, et al., 1955
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W.,
Zur Kenntnis der physikalisch-chemischen Grundlagen der Gewinnung und Zerlegung der Phenolfraktionen von Steinkohlenteer und Braunkohlenschwelteer. IV. Mitteilung Die Dampfdrucke von Phenol und Phenolderivaten,
Brennst.-Chem., 1955, 36, 272-274. [all data]
Chen, Oja, et al., 2006
Chen, Xu; Oja, Vahur; Chan, W. Geoffrey; Hajaligol, Mohammad R.,
Vapor Pressure Characterization of Several Phenolics and Polyhydric Compounds by Knudsen Effusion Method,
J. Chem. Eng. Data, 2006, 51, 2, 386-391, https://doi.org/10.1021/je050293h
. [all data]
Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.,
Uber sublimationswarmen,
Z. Phys. Chem., 1938, 39, 194-208. [all data]
Verevkin and Schick, 2000
Verevkin, Sergey P.; Schick, Christoph,
Substituent Effects on the Benzene Ring. Determination of the Intramolecular Interactions of Substituents in tert -Alkyl-Substituted Catechols from Thermochemical Measurements,
J. Chem. Eng. Data, 2000, 45, 5, 946-952, https://doi.org/10.1021/je0001126
. [all data]
Lee, Chang, et al., 1997
Lee, Ming-Jer; Chang, Yao-Kun; Lin, Ho-mu; Chen, Chang-Hsin,
Solid-Liquid Equilibria for 4-Methoxyphenol with Catechol, Ethylenediamine, or Piperazine,
J. Chem. Eng. Data, 1997, 42, 2, 349-352, https://doi.org/10.1021/je960201b
. [all data]
Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Speirs, M.; Ridyard, J.N.A.,
The electronic structure of substituted benzenes; ab initio calculations and photoelectron spectra for phenol, the methyl- and fluoro-derivatives, and the dihydroxybenzenes,
J. Mol. Struct., 1979, 52, 293. [all data]
Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W.,
Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities,
J. Am. Chem. Soc., 1981, 103, 4017. [all data]
Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B.,
Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria,
J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law 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 Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K 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 ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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