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Benzoic acid, methyl ester

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

Quantity Value Units Method Reference Comment
Deltafgas-269.3 ± 5.1kJ/molEqkGuthrie and Cullimore, 1980 
Deltafgas-299.8kJ/molCcrHall and Baldt, 1971 

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
Deltafliquid-324.3 ± 3.0kJ/molEqkGuthrie and Cullimore, 1980ALS
Deltafliquid-343.5kJ/molCcrHall and Baldt, 1971ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3947.9 ± 2.4kJ/molCcrHall and Baldt, 1971Corresponding «DELTA»fliquid = -343.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
221.3298.15Fuchs, 1979DH
216.5297.Hall and Baldt, 1971DH

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
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil472.4 ± 0.8KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus260.8KN/ABuckingham and Donaghy, 1982BS
Tfus260.7KN/ADozen, Fujishima, et al., 1978Uncertainty assigned by TRC = 0.2 K; TRC
Tfus260.8KN/ADreisbach, 1955Uncertainty assigned by TRC = 0.02 K; TRC
Tfus260.94KN/ADreisbach and Martin, 1949Uncertainty assigned by TRC = 0.05 K; TRC
Tfus260.75KN/ATimmermans and Hennaut-Roland, 1935Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Deltavap52. ± 9.kJ/molAVGN/AAverage of 9 values; Individual data points

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
370.20.032Weast and Grasselli, 1989BS
369. - 371.0.032Buckingham and Donaghy, 1982BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
51.1 ± 0.2360.EBSteele, Chirico, et al., 2002Based on data from 358. - 517. K.; AC
48.5 ± 0.2400.EBSteele, Chirico, et al., 2002Based on data from 358. - 517. K.; AC
45.8 ± 0.2440.EBSteele, Chirico, et al., 2002Based on data from 358. - 517. K.; AC
43.0 ± 0.4480.EBSteele, Chirico, et al., 2002Based on data from 358. - 517. K.; AC
57.2 ± 0.1303.CMaksimuk, Kabo, et al., 1998AC
50.7379.BGKatayama, 1988Based on data from 334. - 428. K.; AC
48.3410.BGKatayama, 1988Based on data from 334. - 428. K.; AC
49.7388.AStephenson and Malanowski, 1987Based on data from 373. - 533. K.; AC
52.8363.BGBaldt and Hall, 1971Based on data from 341. - 433. 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
384.03 - 472.31.95374474.908-232.81Dreisbach and Shrader, 1949Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
14.8260.8ACBlokhin, Paulechka, et al., 2002Based on data from 5. - 320. K.; AC
14.83260.8N/AMaksimuk, Kabo, et al., 1998AC
13.9261.N/ADozen, Fujishima, et al., 1978, 2AC

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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: 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

1-(Dimethoxy-phenylmethyl)-1H-imidazole + Water = 1H-Imidazole + Methyl Alcohol + Benzoic acid, methyl ester

By formula: C12H14N2O2 + H2O = C3H4N2 + CH4O + C8H8O2

Quantity Value Units Method Reference Comment
Deltar-55.48 ± 0.71kJ/molCmGuthrie and Pike, 1987liquid phase; Heat of hydrolysis

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

Benzene, (trimethoxymethyl)- + Water = 2Methyl Alcohol + Benzoic acid, methyl ester

By formula: C10H14O3 + H2O = 2CH4O + C8H8O2

Quantity Value Units Method Reference Comment
Deltar-17.3 ± 0.4kJ/molEqkGuthrie and Cullimore, 1980liquid 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
56. VN/A

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
L - Sharon G. Lias

Data compiled as indicated in comments:
MM - Michael M. Meot-Ner (Mautner)
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

View reactions leading to C8H8O2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.32 ± 0.04eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)850.5kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity819.5kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.18ECDKuhn, Levins, et al., 1968Done at constant temperature, accuracy uncertain: Chen and Wentworth, 1989;; B

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
814.9 ± 0.5Decouzon, Gal, et al., 1996T = 338K; MM

Ionization energy determinations

IE (eV) Method Reference Comment
9.32 ± 0.03PIMcLoughlin and Traeger, 1979LLK
9.48EIElder, Beynon, et al., 1976LLK
9.28PEBehan, Johnstone, et al., 1976LLK
9.4 ± 0.1EIGilbert, Leach, et al., 1973LLK
9.49EIBenoit, 1973LLK
9.35 ± 0.03EIJohnstone and Mellon, 1972LLK
9.40 ± 0.025PEJohnstone and Mellon, 1972LLK
9.35 ± 0.06EIFoffani, Pignataro, et al., 1964RDSH
9.79PECabelli, Cowley, et al., 1982Vertical value; LBLHLM
9.5PEMeeks, Wahlborg, et al., 1981Vertical value; LLK
9.34PEBenoit and Harrison, 1977Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H5+13.9 ± 0.1OCH3+COEIBurgers and Holmes, 1982LBLHLM
C6H5+14.3 ± 0.07OCH3+COEITajima, Azami, et al., 1977LLK
C6H5+14.74CH3O+COEIBenoit, 1973LLK
C6H5+13.82OCH3+COEIJohnstone and Mellon, 1972LLK
C7H5O+10.5 ± 0.1OCH3EIBurgers and Holmes, 1982LBLHLM
C7H5O+10.43OCH3PIMcLoughlin and Traeger, 1979LLK
C7H5O+10.8 ± 0.05OCH3EITajima, Azami, et al., 1977LLK
C7H5O+10.83OCH3EIElder, Beynon, et al., 1976LLK
C7H5O+11.40OCH3EIBenoit, 1973LLK
C7H5O+10.80CH3OEIHowe and Williams, 1969RDSH

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)

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, 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 Chuck Anderson, Aldrich Chemical Co.
NIST MS number 107744

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.


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), Notes

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

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]

Hall and Baldt, 1971
Hall, H.K., Jr.; Baldt, J.H., Thermochemistry of strained-ring bridgehead nitriles and esters, J. Am. Chem. Soc., 1971, 93, 140-145. [all data]

Fuchs, 1979
Fuchs, R., Heat capacities of some liquid aliphatic, alicyclic, and aromatic esters at 298.15 K, J. Chem. Thermodyn., 1979, 11, 959-961. [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]

Dozen, Fujishima, et al., 1978
Dozen, Y.; Fujishima, S.; Shingu, H., Structures and fusion parameters of methoxycarbonyl-benzenes and -naphthalenes, Thermochim. Acta, 1978, 25, 2, 209, https://doi.org/10.1016/0040-6031(78)85008-4 . [all data]

Dreisbach, 1955
Dreisbach, R.R., Physical Properties of Chemical Compounds, Advances in Chemistry Series No. 15, Am. Chem. Soc.: Washington, D. C., 1955. [all data]

Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A., Physical Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 2875-8. [all data]

Timmermans and Hennaut-Roland, 1935
Timmermans, J.; Hennaut-Roland, M., Physical constants of 20 organic compounds. VII. Supplement, J. Chim. Phys. Phys.-Chim. Biol., 1935, 32, 589. [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]

Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A., Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for Methyl Benzoate, Ethyl Benzoate, ( R )-(+)-Limonene, tert -Amyl Methyl Ether, trans -Crotonaldehyde, and Diethylene Glycol, J. Chem. Eng. Data, 2002, 47, 4, 667-688, https://doi.org/10.1021/je0100847 . [all data]

Maksimuk, Kabo, et al., 1998
Maksimuk, Yury V.; Kabo, Gennady J.; Simirsky, Vladimir V.; Kozyro, Alexander A.; Sevruk, Victor M., Standard Enthalpies of Formation of Some Methyl Esters of Benzene Carboxylic Acids, J. Chem. Eng. Data, 1998, 43, 3, 293-298, https://doi.org/10.1021/je970116j . [all data]

Katayama, 1988
Katayama, Hirotake, Vapor pressures of methyl, ethyl, n-propyl, isobutyl, and n-butyl benzoates at reduced pressures, J. Chem. Eng. Data, 1988, 33, 2, 75-77, https://doi.org/10.1021/je00052a002 . [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]

Baldt and Hall, 1971
Baldt, J.H.; Hall, H.K.K., Jr., Thermochemistry of strained-ring bridgehead nitriles and esters, J. Am. Chem. Soc., 1971, 93, 140-145. [all data]

Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A., Vapor Pressure--Temperature Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054 . [all data]

Blokhin, Paulechka, et al., 2002
Blokhin, A.V.; Paulechka, Y.U.; Kabo, G.J.; Kozyro, A.A., Thermodynamic properties of methyl esters of benzoic and toluic acids in the condensed state, The Journal of Chemical Thermodynamics, 2002, 34, 1, 29-55, https://doi.org/10.1006/jcht.2001.0852 . [all data]

Dozen, Fujishima, et al., 1978, 2
Dozen, Yasuhiko; Fujishima, Shizu; Shingu, Haruo, Structures and fusion parameters of methoxycarbonyl-benzenes and -naphthalenes, Thermochimica Acta, 1978, 25, 2, 209-216, https://doi.org/10.1016/0040-6031(78)85008-4 . [all data]

Guthrie and Pike, 1987
Guthrie, J.P.; Pike, D.C., Hydration of acylimidazoles: tetrahedral intermediates in acylimidazole hydrolysis and nucleophilic attack by imidazole on esters. The question of concerted mechanisms for acyl transfers, Can. J. Chem., 1987, 65, 1951-1969. [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]

Kuhn, Levins, et al., 1968
Kuhn, W.F.; Levins, R.J.; Lilly, A.C., Jr., Electron affinities and ionization potentials of phthalate compounds, J. Chem. Phys., 1968, 49, 5550. [all data]

Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E., Experimental Determination of Electron Affinities of Organic Molecules, Mol. Cryst. Liq. Cryst., 1989, 171, 271. [all data]

Decouzon, Gal, et al., 1996
Decouzon, M.; Gal, J.E.; Herreros, M.; Marai, P.C.; Murrell, J.; Todd, J.F.J., On the Use of the Kinetic Method for the Determination of Proton Affinities by Fourier-Transfrom Ion Cyclotron Resonance Mass Spectrometry, Rapid. Comm. Mass Spectrom., 1996, 10, 242. [all data]

McLoughlin and Traeger, 1979
McLoughlin, R.G.; Traeger, J.C., A photoionization study of some benzoyl compounds - thermochemistry of [C7H5O]+ formation, Org. Mass Spectrom., 1979, 14, 434. [all data]

Elder, Beynon, et al., 1976
Elder, J.F.; Beynon, J.H.; Cooks, R.G., The benzoyl ion. Thermochemistry and kinetic energy release, Org. Mass Spectrom., 1976, 11, 415. [all data]

Behan, Johnstone, et al., 1976
Behan, J.M.; Johnstone, R.A.W.; Bentley, T.W., An evaluation of empirical methods for calculating the ionization potentials of substituted benzenes, Org. Mass Spectrom., 1976, 11, 207. [all data]

Gilbert, Leach, et al., 1973
Gilbert, J.R.; Leach, W.P.; Miller, J.R., Ionisation appearance potential measurements in arene chromium tricarbonyls, J. Organomet. Chem., 1973, 49, 219. [all data]

Benoit, 1973
Benoit, F., The benzoyl cation: The participation of isolated electronic excited states in the dissociation of molecular ions of the form [C6H5COX]+, Org. Mass Spectrom., 1973, 7, 1407. [all data]

Johnstone and Mellon, 1972
Johnstone, R.A.W.; Mellon, F.A., Electron-impact ionization and appearance potentials, J. Chem. Soc. Faraday Trans. 2, 1972, 68, 1209. [all data]

Foffani, Pignataro, et al., 1964
Foffani, A.; Pignataro, S.; Cantone, B.; Grasso, F., Ionization potentials and substituent effects for aromatic carbonyl compounds, Z. Physik. Chem. (Frankfurt), 1964, 42, 221. [all data]

Cabelli, Cowley, et al., 1982
Cabelli, D.E.; Cowley, A.H.; Lagowski, J.J., The bonding in some bis(arene)chromium compounds as indicated by U. V. photoelectron zpectroscopy, Inorg. Chim. Acta, 1982, 57, 195. [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]

Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [all data]

Burgers and Holmes, 1982
Burgers, P.C.; Holmes, J.L., Metastable ion studies. XIII. The measurement of appearance energies of metastable peaks, Org. Mass Spectrom., 1982, 17, 123. [all data]

Tajima, Azami, et al., 1977
Tajima, S.; Azami, T.; Tsuchiya, T., An investigation of the decomposition of the common intermediate ions produced by electron impact, Org. Mass Spectrom., 1977, 12, 24. [all data]

Howe and Williams, 1969
Howe, I.; Williams, D.H., Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes, J. Am. Chem. Soc., 1969, 91, 7137. [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), References