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Benzeneacetic acid

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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltacsolid-931.33 ± 0.19kcal/molCcbWrede, 1911Corresponding «DELTA»fsolid = -94.34 kcal/mol (simple calculation by NIST; no Washburn corrections)
Deltacsolid-931.5kcal/molCcbAuwers and Roth, 1910Corresponding «DELTA»fsolid = -94.2 kcal/mol (simple calculation by NIST; no Washburn corrections)
Deltacsolid-933.4kcal/molCcbFischer and Wrede, 1904Heat of combustion corrected for pressure; Corresponding «DELTA»fsolid = -92.3 kcal/mol (simple calculation by NIST; no Washburn corrections)
Deltacsolid-934.5kcal/molCcbLemoult, 1904Corresponding «DELTA»fsolid = -91.1 kcal/mol (simple calculation by NIST; no Washburn corrections)

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, Kenneth Kroenlein director
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil538.7KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Tfus348.KN/AHenne and Hill, 1943Uncertainty assigned by TRC = 2. K; TRC
Tfus349.15KN/AAdams and Marshall, 1928Uncertainty assigned by TRC = 1. K; TRC
Tfus350.KN/ARobertson, 1902Uncertainty assigned by TRC = 2. K; TRC
Tfus348.05KN/ABruner, 1894Uncertainty assigned by TRC = 0.6 K; TRC
Quantity Value Units Method Reference Comment
Deltavap18.9 ± 0.07kcal/molGSRoux *, Temprado, et al., 2004Based on data from 353. - 392. K.; AC
Quantity Value Units Method Reference Comment
Deltasub22.3 ± 0.07kcal/molGSRoux *, Temprado, et al., 2004Based on data from 307. - 339. K.; AC
Deltasub23.7 ± 0.1kcal/molMEMonte and Hillesheim, 2001Based on data from 305. - 321. K.; AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
15.5385.AStephenson and Malanowski, 1987Based on data from 370. - 539. K.; AC

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
23.6 ± 0.1313.MEMonte and Hillesheim, 2001Based on data from 305. - 321. K.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Method Reference Comment
3.63349.2N/AGracin and Rasmuson, 2002AC
3.94350.8N/AMonte and Hillesheim, 2001AC
3.463349.9DSCAcree, 1991There is a large discrepancy between the value of 32.0 kJ/mole and the other reported literature values. Reference Sharma, Kant, et al., 2003 quotes a literature value of 32.0 kJ/mole; however, the authors do not provide the source of the cited literature value.; AC

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

C8H7O2- + Hydrogen cation = Benzeneacetic acid

By formula: C8H7O2- + H+ = C8H8O2

Quantity Value Units Method Reference Comment
Deltar341.5 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar341.1 ± 2.1kcal/molG+TSJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar334.5 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar334.1 ± 2.0kcal/molIMREJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale

Gas phase ion energetics 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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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

View reactions leading to C8H8O2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.26eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
~8.26PEKlasinc, Kovac, et al., 1983LBLHLM
8.26PEMeeks, Wahlborg, et al., 1981LLK
8.72PEKlasinc, Kovac, et al., 1983Vertical value; LBLHLM
9.1PEMeeks, Wahlborg, et al., 1981Vertical value; LLK

De-protonation reactions

C8H7O2- + Hydrogen cation = Benzeneacetic acid

By formula: C8H7O2- + H+ = C8H8O2

Quantity Value Units Method Reference Comment
Deltar341.5 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Deltar341.1 ± 2.1kcal/molG+TSJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar334.5 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Deltar334.1 ± 2.0kcal/molIMREJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

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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: 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 NIST Mass Spectrometry Data Center
NIST MS number 352514

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

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, 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 Meiggs and Miller, 1972
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. 16425
Instrument Beckman DK-2a
Melting point 75.5-76.5

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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.

Wrede, 1911
Wrede, F., Uber die Bestimmung von Berbrennungswarmen mittels der kalorimetrischen Bombe unter Benutzung des Platinwiderstandsthermometers, Z. Phys. Chem. (Leipzig), 1911, 81-94. [all data]

Auwers and Roth, 1910
Auwers, K.; Roth, W.A., Thermochemische Untersuchungen. I. Uber Beziehungen zwischen Konstitution und Verbrennungswarme ungesattigter Verbindungen, Justus Liebigs Ann. Chem., 1910, 239-248. [all data]

Fischer and Wrede, 1904
Fischer, E.; Wrede, F., Uber die Verbrennungswarme einiger organischer Verbindungen, Sitzungsber. Dtsch. Akad. Wiss. Berlin Kl. Math. Phys. Tech., 1904, 687-715. [all data]

Lemoult, 1904
Lemoult, M.P., Remarques sur une serie recenie de determinations calorimetriques, Compt. Rend., 1904, 663-635. [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]

Henne and Hill, 1943
Henne, A.L.; Hill, P., The Preparatioon of Aldehydes, Ketones, and Acids by Ozone Oxidation, J. Am. Chem. Soc., 1943, 65, 752-4. [all data]

Adams and Marshall, 1928
Adams, R.; Marshall, J.R., The Use of Platinum-Oxide Platinum Black in the Catalytic Reduction of Aromatic Hydrocarbons XVII., J. Am. Chem. Soc., 1928, 50, 1970. [all data]

Robertson, 1902
Robertson, P.W., Atomic and molecular heats of fusion., J. Chem. Soc., 1902, 81, 1233. [all data]

Bruner, 1894
Bruner, L., The heats of fusion of some organic compounds, Ber. Dtsch. Chem. Ges., 1894, 27, 2102. [all data]

Roux *, Temprado, et al., 2004
Roux *, Maria Victoria; Temprado, Manuel; Notario, Rafael; Verevkin, Sergey P.; Emel'yanenko, Vladimir N.; Demasters, Douglas E.; Liebman, Joel F., The energetics of naphthalene derivatives, III: phenylacetic acid and the isomeric 1- and 2-naphthylacetic acids, Molecular Physics, 2004, 102, 18, 1909-1917, https://doi.org/10.1080/00268970412331284262 . [all data]

Monte and Hillesheim, 2001
Monte, Manuel J.S.; Hillesheim, Dorothea M., Thermodynamic Study on the Sublimation of 2-Phenylacetic, 4-Phenylbutyric, and 5-Phenylvaleric Acid, J. Chem. Eng. Data, 2001, 46, 6, 1601-1604, https://doi.org/10.1021/je010153h . [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]

Gracin and Rasmuson, 2002
Gracin, Sandra; Rasmuson, Åke C., Solubility of Phenylacetic Acid, p -Hydroxyphenylacetic Acid, p -Aminophenylacetic Acid, p -Hydroxybenzoic Acid, and Ibuprofen in Pure Solvents, J. Chem. Eng. Data, 2002, 47, 6, 1379-1383, https://doi.org/10.1021/je0255170 . [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]

Sharma, Kant, et al., 2003
Sharma, B.L.; Kant, Rajesh; Sharma, Ritu; Tandon, Sonika, Deviations of binary organic eutectic melt systems, Materials Chemistry and Physics, 2003, 82, 1, 216-224, https://doi.org/10.1016/S0254-0584(03)00199-8 . [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]

Jinfeng, Topsom, et al., 1988
Jinfeng, C.; Topsom, R.D.; Headley, A.D.; Koppel, I.; Mishima, M.; Taft, R.W.; Veji, S., Acidities of Substituted Acetic Acids, J. Mol. Struct., 1988, 168, 141, https://doi.org/10.1016/0166-1280(88)80349-X . [all data]

Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H., Photoelectron spectra of acenes. Electronic structure and substituent effects, Pure Appl. Chem., 1983, 55, 289. [all data]

Meeks, Wahlborg, et al., 1981
Meeks, J.; Wahlborg, A.; McGlynn, S.P., Photoelectron spectroscopy of carbonyls: Benzoic acid and its derivatives, J. Electron Spectrosc. Relat. Phenom., 1981, 22, 43. [all data]

Meiggs and Miller, 1972
Meiggs, T.O.; Miller, S.I., J. Am. Chem. Soc., 1972, 94, 1989. [all data]


Notes

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