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1,2-Benzenediol

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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
Deltafgas-274.8 ± 1.2kJ/molCcrSabbah and Buluku, 1991«DELTA»Hfusion =15.00±0.34 kJ/mol; ALS
Deltafgas-267.5 ± 1.9kJ/molCcbRibeiro Da Silva and Ribeiro Da Silva, 1984ALS
Deltafgas-271.6 ± 2.0kJ/molCcbFinch, Gardner, et al., 1983ALS
Deltafgas-262.5kJ/molN/APushin, 1954Value computed using «DELTA»fHsolid° value of -344.0 kj/mol from Pushin, 1954 and «DELTA»subH° 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
34.3950.Kudchadker S.A., 1979GT
45.32100.
62.77150.
82.10200.
110.62273.15
120.09298.15
120.78300.
155.47400.
183.90500.
206.30600.
223.91700.
237.92800.
249.27900.
258.601000.
266.381100.
272.931200.
278.491300.
283.251400.
287.351500.

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
Deltafsolid-362.3 ± 1.1kJ/molCcrSabbah and Buluku, 1991«DELTA»Hfusion =15.00±0.34 kJ/mol; ALS
Deltafsolid-354.1 ± 1.1kJ/molCcbRibeiro Da Silva and Ribeiro Da Silva, 1984ALS
Deltafsolid-353.1 ± 1.1kJ/molCcbFinch, Gardner, et al., 1983ALS
Deltafsolid-344.kJ/molCcbPushin, 1954Author's hf298_condensed=-83.8 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-2856.3 ± 1.1kJ/molCcrSabbah and Buluku, 1991«DELTA»Hfusion =15.00±0.34 kJ/mol; Corresponding «DELTA»fsolid = -362.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-2864.5 ± 0.8kJ/molCcbRibeiro Da Silva and Ribeiro Da Silva, 1984Corresponding «DELTA»fsolid = -354.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-2865.49 ± 0.74kJ/molCcbFinch, Gardner, et al., 1983Corresponding «DELTA»fsolid = -353.06 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-2874.kJ/molCcbPushin, 1954Author's hf298_condensed=-83.8 kcal/mol; Corresponding «DELTA»fsolid = -344. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-2862.kJ/molCcbBarker, 1925Author was aware that data differs from previously reported values; Corresponding «DELTA»fsolid = -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
140.17298.15Bret-Dibat and Lichanot, 1989T = 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
140.6298.15Ueberreiter and Orthmann, 1950T = 293 to 368 K. Equation only.; DH
156.9323.Satoh and Sogabe, 1941T = 0 to 100°C. Mean value.; DH
132.2298.Andrews, Lynn, et al., 1926T = 22 to 200°C.; DH
139.3297.9Andrews, 1926T = 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
Tboil518.2KN/AWeast and Grasselli, 1989BS
Tboil513.KN/ABuckingham and Donaghy, 1982BS
Tboil518.8KN/AKrupatkin and Rozhentsova, 1971Uncertainty assigned by TRC = 0.4 K; TRC
Tboil519.05KN/ALecat, 1943Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus377. ± 1.KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple377.5KN/AAndrews, Lynn, et al., 1926, 2Uncertainty assigned by TRC = 0.2 K; obtained from cooling curve in absence of air; TRC
Quantity Value Units Method Reference Comment
Deltavap71.9 ± 0.8kJ/molGSVerevkin and Kozlova, 2008Based on data from 378. - 389. K.; AC
Quantity Value Units Method Reference Comment
Deltasub86. ± 4.kJ/molAVGN/AAverage of 7 values; Individual data points

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
63.1410.AStephenson and Malanowski, 1987Based on data from 395. - 519. K.; AC
61.2393.GCKundel, Lille, et al., 1975Based on data from 378. - 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 - 518.75.50332713.153-23.96von Terres, Gebert, et al., 1955Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
80.0 ± 0.5302.N/AChen, Oja, et al., 2006Based on data from 295. - 310. K.; AC
81. ± 2.309.VWolf and Weghofer, 1938ALS

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
22.000376.85N/ABret-Dibat and Lichanot, 1989DH
22.87377.6N/AVerevkin and Kozlova, 2008AC
18.55377.6N/AVerevkin and Schick, 2000AC
22.54377.7DSCLee, Chang, et al., 1997AC
22.01376.9N/ABret-Dibat and Lichanot, 1989AC
22.760337.5N/AAndrews, Lynn, et al., 1926DH
22.76377.5CAndrews, Lynn, et al., 1926AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
58.376.85Bret-Dibat and Lichanot, 1989DH
60.3337.5Andrews, Lynn, et al., 1926DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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: John E. Bartmess

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

C6H5O2- + Hydrogen cation = 1,2-Benzenediol

By formula: C6H5O2- + H+ = C6H6O2

Quantity Value Units Method Reference Comment
Deltar1420. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1422. ± 11.kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1392. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1393. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

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) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 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)

H (mol/kg*bar) d(ln(kH))/d(1/T) (K) Method Reference
4600. VN/A

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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
8.15PEPalmer, Moyes, et al., 1979LLK
8.56PEPalmer, Moyes, et al., 1979Vertical value; LLK

De-protonation reactions

C6H5O2- + Hydrogen cation = 1,2-Benzenediol

By formula: C6H5O2- + H+ = C6H6O2

Quantity Value Units Method Reference Comment
Deltar1420. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1422. ± 11.kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar1392. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1393. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, 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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Mass 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-1681
NIST MS number 227771

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Dewar, Kubba, et al., 1958
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 1289
Instrument n.i.g.
Melting point 105
Boiling point 245

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

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]

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]

Dewar, Kubba, et al., 1958
Dewar, M.J.S.; Kubba, V.P.; Pettit, R., New heteroaromatic compounds. Part II. Boron compounds isoconjugate with indole, 2:3-benzofuran, and thionaphthen, J. Chem. Soc., 1958, 3076-3079. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References