Benzoic acid, 3-methyl-

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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Δfgas-78.37 ± 0.33kcal/molCcbColomina, Jimenez, et al., 1986see Colomina, Boned, et al., 1961; ALS
Δfgas-78.66kcal/molN/ACorral, 1960Value computed using ΔfHsolid° value of -426.1±1.0 kj/mol from Corral, 1960 and ΔsubH° value of 97.0 kj/mol from Colomina, Jimenez, et al., 1986.; DRB

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
Δfsolid-101.6 ± 0.33kcal/molCcbColomina, Jimenez, et al., 1986see Colomina, Boned, et al., 1961; ALS
Δfsolid-101.84 ± 0.23kcal/molCcbCorral, 1960ALS
Quantity Value Units Method Reference Comment
Δcsolid-924.1 ± 0.2kcal/molCcbColomina, Jimenez, et al., 1986see Colomina, Boned, et al., 1961; Corresponding Δfsolid = -101.6 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-923.84 ± 0.19kcal/molCcbCorral, 1960Corresponding Δfsolid = -101.83 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-923.1kcal/molCcbAuwers and Roth, 1910Corresponding Δfsolid = -102.6 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
39.10298.Andrews, Lynn, et al., 1926T = 22 to 170 C.; 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
Tboil536.2KN/AAldrich Chemical Company Inc., 1990BS
Quantity Value Units Method Reference Comment
Tfus384.KN/ASugunan and Thomas, 1993Uncertainty assigned by TRC = 1.5 K; TRC
Tfus384.4KN/ANoyce and Nagle, 1953Uncertainty assigned by TRC = 2. K; TRC
Tfus381.9KN/AAndrews, Lynn, et al., 1926, 2Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Δsub23.2 ± 0.07kcal/molMEColomina, Jimenez, et al., 1986, 2Based on data from 303. to 323. K.; AC
Δsub23.2 ± 0.07kcal/molVColomina, Jimenez, et al., 1986see Colomina, Boned, et al., 1961; ALS
Δsub23.2kcal/molN/AColomina, Jimenez, et al., 1986DRB

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
15.0503.AStephenson and Malanowski, 1987Based on data from 473. to 533. K. See also Mullayanov, Galagan, et al., 1970.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
3.760381.9Acree, 1991AC
3.7596381.9Andrews, Lynn, et al., 1926DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
9.85381.9Andrews, 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

C8H7O2- + Hydrogen cation = Benzoic acid, 3-methyl-

By formula: C8H7O2- + H+ = C8H8O2

Quantity Value Units Method Reference Comment
Δr340.6 ± 2.1kcal/molG+TSKebarle and McMahon, 1977gas phase
Δr340.4 ± 2.1kcal/molG+TSDecouzon, Exner, et al., 1996gas phase; Relative to benzoate at 333.0 kcal/mol
Quantity Value Units Method Reference Comment
Δr333.6 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase
Δr333.4 ± 2.0kcal/molIMREDecouzon, Exner, et al., 1996gas phase; Relative to benzoate at 333.0 kcal/mol

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:
HL - Edward P. Hunter and Sharon G. Lias

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 C8H8O2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)198.3kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity190.9kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.4 ± 0.2EIBenoit, 1973LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H7+12.5 ± 0.2COOHEIBenoit, 1973LLK
C8H7O+12.4 ± 0.2OHEIBenoit, 1973LLK

De-protonation reactions

C8H7O2- + Hydrogen cation = Benzoic acid, 3-methyl-

By formula: C8H7O2- + H+ = C8H8O2

Quantity Value Units Method Reference Comment
Δr340.6 ± 2.1kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Δr340.4 ± 2.1kcal/molG+TSDecouzon, Exner, et al., 1996gas phase; Relative to benzoate at 333.0 kcal/mol; B
Quantity Value Units Method Reference Comment
Δr333.6 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B
Δr333.4 ± 2.0kcal/molIMREDecouzon, Exner, et al., 1996gas phase; Relative to benzoate at 333.0 kcal/mol; B

IR 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: 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 Sadtler Research Labs Under US-EPA Contract
State gas

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, 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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Due to licensing restrictions, this spectrum cannot be downloaded.

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, 1998.
NIST MS number 291073

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 Lang (editor), 1969
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. 19062
Instrument Unicam SP 700
Melting point 110-111

References

Go To: Top, Gas phase thermochemistry data, 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.

Colomina, Jimenez, et al., 1986
Colomina, M.; Jimenez, P.; Roux, M.V.; Turrion, C., Propiedades termoquimicas de derivados del acido benzoico. XIII. Presiones de vapor y entalpias de sublimacion y formacion de los acidos toluicos, An. Quim., 1986, 82, 126-130. [all data]

Colomina, Boned, et al., 1961
Colomina, M.; Boned, M.L.; Turrion, C., Investigaciones termoquimicas sobre los acidos alquilbenzoicos. I. Acidos toluicos, An. Fis. Quim., 1961, 57, 655-664. [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]

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]

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]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Sugunan and Thomas, 1993
Sugunan, S.; Thomas, B., Salting Coefficients of 2-, 3-, and 4-Methylbenzoic Acids, J. Chem. Eng. Data, 1993, 38, 520-1. [all data]

Noyce and Nagle, 1953
Noyce, D.S.; Nagle, R.J., Studies of Configuration II. The Configurations of the 3-Methylcyclohexylamines, J. Am. Chem. Soc., 1953, 75, 127. [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]

Colomina, Jimenez, et al., 1986, 2
Colomina, M.; Jimenez, P.; Roux, M.V.; Turrion, C., Propiedades termoquimicas de derivados del acido benzoico. XIII. Presiones de vapor y entalpias de sublimacion y formacion de los acidos toluicos, An. Quim., 1986, 82, 126. [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]

Mullayanov, Galagan, et al., 1970
Mullayanov, F.I.; Galagan, G.V.; Buz'ko, M.F.; Churkin, Yu.V.; Shiryaeva, A.A., Tr. Nauch. Issled. Inst. Neftekhim. Proizvod., 1970, 2, 95. [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]

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]

Decouzon, Exner, et al., 1996
Decouzon, M.; Exner, O.; Gal, J.-F.; Maria, P.-C., Non-classical Buttressing Effect: Gas-phase Ionization of Some Methyl Substituted Benzoic Acids, J. Chem. Soc. Perkin Trans., 1996, 2, 4, 475, https://doi.org/10.1039/p29960000475 . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Benoit, 1973
Benoit, F., Substituent effects in mass spectrometry. III. Substituent effects in the dissociation of the molecular ions of para and meta subtituted benzoic acids, Org. Mass Spectrom., 1973, 7, 295. [all data]

Lang (editor), 1969
Lang (editor), L., Absorption Spectra in the Ultraviolet and Visible Region, 1969, 12, 63. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, 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