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Benzoic acid

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Gas 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 by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
103.47298.15Stull D.R., 1969These values were calculated from preliminary assignment of vibrational frequencies. Statistical calculation [ Ali N., 1983] seems to be erroneous.
104.01300.
138.36400.
170.54500.
196.73600.
217.82700.
234.89800.
248.95900.
260.661000.

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
Deltacliquid-3227.00 ± 0.20kJ/molCcbGundry, Harrop, et al., 1969Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -3225.73 kJ/mol; Corresponding «DELTA»fliquid = -385.06 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
Deltafsolid-384.8 ± 0.50kJ/molCcbCorral, 1960ALS
Deltafsolid-386.kJ/molCcbLandrieu, Baylocq, et al., 1929ALS
Quantity Value Units Method Reference Comment
Deltacsolid-3228. ± 4.kJ/molAVGN/AAverage of 17 out of 18 values; Individual data points
Quantity Value Units Method Reference Comment
solid,1 bar165.71J/mol*KN/AKaji, Tochigi, et al., 1993DH
solid,1 bar167.73J/mol*KN/AArvidsson, Falk, et al., 1976DH
solid,1 bar167.59J/mol*KN/AFurukawa, McCoskey, et al., 1951DH
solid,1 bar167.82J/mol*KN/ADavies and Staveley, 1957DH
solid,1 bar170.7J/mol*KN/AParks, Huffman, et al., 1933Extrapolation below 90 K, 59.25 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
259.413.Pacor, 1967DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
147.78300.Kaji, Tochigi, et al., 1993T = 19 to 312 K. Unsmoothed experimental datum.; DH
147.03298.902Sorai, Kaji, et al., 1992T = 15 to 305 K. Unsmoothed experimental datum.; DH
146.23296.29Moriya, Matsuo, et al., 1982T = 13 to 355 K. NBS SRM 29.; DH
146.65298.15Shakirov and Lyubarskii, 1980T = 20 to 300 K.; DH
146.79298.15Arvidsson, Falk, et al., 1976T = 6 to 341 K.; DH
147.07299.62Tatsumi, Matsuo, et al., 1975T = 12 to 304 K.; DH
149.301.Mosselman, Mourik, et al., 1974One temperature, T = 5 K. Value 5 J/mol*K.; DH
146.80298.15Konicek, Suurkuusk, et al., 1971DH
167.40298.15Justice, 1969As check on system. Only value at 298 K given.; DH
147.14299.99Suga and Seki, 1965T = 13 to 300 K. Value is unsmoothed experimental datum.; DH
130.340.David, 1964T = 298 to 373 K. Mean value. T = uncertain.; DH
146.31298.15Kolesov, Seregin, et al., 1962T = 22 to 310 K.; DH
147.02298.15Davies and Staveley, 1957T = 20 to 298 K.; DH
149.79298.15Popov and Kolesov, 1956T = 80 to 300 K.; DH
146.81298.15Ginnings and Furukawa, 1953T = 14 to 410 K.; DH
146.81298.15Furukawa, McCoskey, et al., 1951T = 13 to 410 K.; DH
160.2323.Satoh and Sogabe, 1939T = 0 to 100 C. Mean value.; DH
145.10295.1Parks, Huffman, et al., 1933T = 93 to 295 K. Value is unsmoothed experimental datum.; DH
155.2298.Andrews, Lynn, et al., 1926T = 22 to 200 C.; DH

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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

benzoate anion + Hydrogen cation = Benzoic acid

By formula: C7H5O2- + H+ = C7H6O2

Quantity Value Units Method Reference Comment
Deltar1423. ± 9.2kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1423. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase; Recalculated from data in paper; error in Table vs. ladder; B
Deltar1423. ± 9.2kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar1393. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1393. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; Recalculated from data in paper; error in Table vs. ladder; B
Deltar1394. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase; B

Bromine anion + Benzoic acid = (Bromine anion bullet Benzoic acid)

By formula: Br- + C7H6O2 = (Br- bullet C7H6O2)

Quantity Value Units Method Reference Comment
Deltar76.6 ± 7.5kJ/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
Deltar84.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar41. ± 4.2kJ/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
41.423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

Water + Benzoyl chloride = Benzoic acid + Hydrogen chloride

By formula: H2O + C7H5ClO = C7H6O2 + HCl

Quantity Value Units Method Reference Comment
Deltar-34.04 ± 0.21kJ/molCmMoselhy and Pritchard, 1975liquid phase; solvent: Diphenyl-ether; see Carson, Pritchard, et al., 1950 and Davies, Dunning, et al., 1972; ALS
Deltar-101.9kJ/molCmCarson, Pritchard, et al., 1950liquid phase; Heat of hydrolysis; ALS

Benzaldehyde + perbenzoic acid = 2Benzoic acid

By formula: C7H6O + C7H6O3 = 2C7H6O2

Quantity Value Units Method Reference Comment
Deltar-316. ± 13.kJ/molCmBriner and Chastonay, 1954liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -317. ± 13. kJ/mol; ALS

Benzoyl bromide + Water = Hydrogen bromide + Benzoic acid

By formula: C7H5BrO + H2O = HBr + C7H6O2

Quantity Value Units Method Reference Comment
Deltar-113.1kJ/molCmCarson, Pritchard, et al., 1950liquid phase; Heat of hydrolysis; ALS

Benzoyl iodide + Water = Hydrogen iodide + Benzoic acid

By formula: C7H5IO + H2O = HI + C7H6O2

Quantity Value Units Method Reference Comment
Deltar-102.4kJ/molCmCarson, Pritchard, et al., 1950liquid phase; Heat of hydrolysis; ALS

Water + Benzoic acid, methyl ester = Benzoic acid + Methyl Alcohol

By formula: H2O + C8H8O2 = C7H6O2 + CH4O

Quantity Value Units Method Reference Comment
Deltar-73.0 ± 1.9kJ/molEqkGuthrie and Cullimore, 1980liquid phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Stull D.R., 1969
Stull D.R., Jr., The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]

Ali N., 1983
Ali N., Thermodynamic functions of the benzoic acid, phthalic acid and salicylic acid, Indian J. Phys., 1983, B57, 413-419. [all data]

Gundry, Harrop, et al., 1969
Gundry, H.A.; Harrop, D.; Head, A.J.; Lewis, G.B., Thermodynamic properties of organic oxygen compounds. 21. Enthalpies of combustion of benzoic acid, pentan-1-ol, octan-1-ol, and hexadecan-1-ol, J. Chem. Thermodyn., 1969, 1, 321-332. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Corral, 1960
Corral, L.B., Investigaciones termoquimicas sobre los acidos toluicos y dimetilbenzoicos, Rev. R. Acad. Cienc., 1960, 54, 365-403. [all data]

Landrieu, Baylocq, et al., 1929
Landrieu, P.; Baylocq, F.; Johnson, J.R., Etude thermochimique dans la serie furanique, Bull. Soc. Chim. France, 1929, 45, 36-49. [all data]

Kaji, Tochigi, et al., 1993
Kaji, K.; Tochigi, K.; Misawa, Y.; Suzuki, T., An adiabatic calorimeter for samples of mass less than 0.1 g and heat capacity measurements on benzoic acid at temperatures from 19 K to 312 K, J. Chem. Thermodynam., 1993, 25(6), 699-709. [all data]

Arvidsson, Falk, et al., 1976
Arvidsson, K.; Falk, B.; Sunner, S., A small sample low temperature adiabatic heat capacity calorimeter with an automatic data acquisition system, Chem. Scr., 1976, 10, 193-200. [all data]

Furukawa, McCoskey, et al., 1951
Furukawa, G.T.; McCoskey, R.E.; King, G.J., Calorimetric properties of benzoic acid from 0 to 410K, J. Res., 1951, NBS 47, 256-261. [all data]

Davies and Staveley, 1957
Davies, T.; Staveley, L.A.K., The behaviour of the ammonium ion in the ammonium salt of tetraphenylboron by comparison of the heat capacities of the ammonium, rubidium, and potassium salts, Trans. Faraday Soc., 1957, 53, 19-30. [all data]

Parks, Huffman, et al., 1933
Parks, G.S.; Huffman, H.M.; Barmore, M., Thermal data on organic compounds. XI. The heat capacities, entropies and free energies of ten compounds containing oxygen or nitrogen. J. Am. Chem. Soc., 1933, 55, 2733-2740. [all data]

Pacor, 1967
Pacor, P., Applicability of the DuPont 900 DTA apparatus in quantitative differential thermal analysis, Anal. Chim. Acta, 1967, 37, 200-208. [all data]

Sorai, Kaji, et al., 1992
Sorai, M.; Kaji, K.; Kaneko, Y., An automated adiabatic calorimeter for the temperature range 13 K to 530 K The heat capacities for benzoic acid from 15 K to 305 K and of synthetic sapphire from 60 K to 505 K, J. Chem. Thermodynam., 1992, 24(2), 167-180. [all data]

Moriya, Matsuo, et al., 1982
Moriya, K.; Matsuo, T.; Suga, H., Low temperature adiabatic calorimeter with a built-in cryo-refrigerator, J. Chem. Thermodynam., 1982, 14, 1143-1148. [all data]

Shakirov and Lyubarskii, 1980
Shakirov, R.F.; Lyubarskii, M.V., Low-temperature heat capacity and thermodynamic functions of methyl trichlorothioacrylate, SPSTL Deposited Publication 3 KhP-D80, 1980, 19p. [all data]

Tatsumi, Matsuo, et al., 1975
Tatsumi, M.; Matsuo, T.; Suga, H.; Seki, S., An adiabatic calorimeter for high-resolution heat capacity measurements in the temperature range from 12 to 300 K, Bull. Chem. Soc. Japan, 1975, 48, 3060-3066. [all data]

Mosselman, Mourik, et al., 1974
Mosselman, C.; Mourik, J.; Dekker, H., Enthalpies of phase change and heat capacities of some long-chain alcohols. Adiabatic semi-microcalorimeter for studies of polymorphism, J. Chem. Thermodynam., 1974, 6, 477-487. [all data]

Konicek, Suurkuusk, et al., 1971
Konicek, J.; Suurkuusk, J.; Wadso, I., A precise drop heat capacity calorimeter for small samples, Chemica Scripta, 1971, 1, 217-220. [all data]

Justice, 1969
Justice, B.H., Low temperature thermodynamic properties of aluminum trichloride, J. Chem. Eng. Data, 1969, 14, 4-5. [all data]

Suga and Seki, 1965
Suga, H.; Seki, S., An automatic adiabatic calorimeter for low temperatures. The heat capacity of standard benzoic acid, Bull. Chem. Soc. Japan, 1965, 38, 1000-1006. [all data]

David, 1964
David, D.J., Determination of specific heat and heat of fusion by differential thermal analysis. Study of theory and operating parameters, Anal. Chem., 1964, 36, 2162-2166. [all data]

Kolesov, Seregin, et al., 1962
Kolesov, V.P.; Seregin, E.A.; Skuratov, S.M., Adiabatic calorimeter of small volume for the determination of true heat capacity over the range 12-340K, Zhur. Fiz. Khim., 1962, 36, 647-651. [all data]

Popov and Kolesov, 1956
Popov, M.M.; Kolesov, V.P., Determination of the true specific heat of solid substances at low temperatures, Zhur. Obshch. Khim., 1956, 26, 2385-2393. [all data]

Ginnings and Furukawa, 1953
Ginnings, D.C.; Furukawa, G.T., Heat capacity standards for the range 14 to 1200°K, J. Am. Chem. Soc., 1953, 75, 522-527. [all data]

Satoh and Sogabe, 1939
Satoh, S.; Sogabe, T., The specific heats of some solid aromatic acids and their ammonium salts and the atomic heat of nitrogen, Sci. Pap. Inst. Phys. Chem. Res. (Tokyo), 1939, 36, 449-457. [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]

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]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P., Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria, Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092 . [all data]

Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P., Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-, J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014 . [all data]

Moselhy and Pritchard, 1975
Moselhy, G.M.; Pritchard, H.O., The thermochemistry of the chloro-benzoyl chlorides, J. Chem. Thermodyn., 1975, 7, 977-982. [all data]

Carson, Pritchard, et al., 1950
Carson, A.S.; Pritchard, H.O.; Skinner, H.A., The heats of hydrolysis of the benzoyl halides, J. Chem. Soc., 1950, 656-659. [all data]

Davies, Dunning, et al., 1972
Davies, J.V.; Dunning, B.K.; Pritchard, H.O., The enthalpy of formation of benzoyl chloride, J. Chem. Thermodyn., 1972, 4, 731-737. [all data]

Briner and Chastonay, 1954
Briner, E.; Chastonay, P., Etude thermochemique de l'autoxydation de Valdehyde benzoique, Helv. Chim. Acta, 1954, 238, 539-541. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Guthrie and Cullimore, 1980
Guthrie, J.P.; Cullimore, P.A., Effect of the acyl substituent on the equilibrium constant for hydration of esters, Can. J. Chem., 1980, 58, 1281-1294. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References