Benzoic acid, methyl ester
- Formula: C8H8O2
- Molecular weight: 136.1479
- IUPAC Standard InChIKey: QPJVMBTYPHYUOC-UHFFFAOYSA-N
- CAS Registry Number: 93-58-3
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Methyl benzoate; Clorius; Methyl benzenecarboxylate; Niobe oil; Oil of Niobe; Essence of niobe; Methylester kyseliny benzoove; Oxidate le; UN 2938; Methyl ester of benzoic acid; Oniobe oil; NSC 9394
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -324.3 ± 3.0 | kJ/mol | Eqk | Guthrie and Cullimore, 1980 | ALS |
ΔfH°liquid | -343.5 | kJ/mol | Ccr | Hall and Baldt, 1971 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3947.9 ± 2.4 | kJ/mol | Ccr | Hall and Baldt, 1971 | Corresponding ΔfHºliquid = -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 |
---|---|---|---|
221.3 | 298.15 | Fuchs, 1979 | DH |
216.5 | 297. | Hall and Baldt, 1971 | DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, 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:
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 |
---|---|---|---|---|---|
Tboil | 472.4 ± 0.8 | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 260.8 | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tfus | 260.7 | K | N/A | Dozen, Fujishima, et al., 1978 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 260.8 | K | N/A | Dreisbach, 1955 | Uncertainty assigned by TRC = 0.02 K; TRC |
Tfus | 260.94 | K | N/A | Dreisbach and Martin, 1949 | Uncertainty assigned by TRC = 0.05 K; TRC |
Tfus | 260.75 | K | N/A | Timmermans and Hennaut-Roland, 1935 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 52. ± 9. | kJ/mol | AVG | N/A | Average of 9 values; Individual data points |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
370.2 | 0.032 | Weast and Grasselli, 1989 | BS |
369. to 371. | 0.032 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
51.1 ± 0.2 | 360. | EB | Steele, Chirico, et al., 2002 | Based on data from 358. to 517. K.; AC |
48.5 ± 0.2 | 400. | EB | Steele, Chirico, et al., 2002 | Based on data from 358. to 517. K.; AC |
45.8 ± 0.2 | 440. | EB | Steele, Chirico, et al., 2002 | Based on data from 358. to 517. K.; AC |
43.0 ± 0.4 | 480. | EB | Steele, Chirico, et al., 2002 | Based on data from 358. to 517. K.; AC |
57.2 ± 0.1 | 303. | C | Maksimuk, Kabo, et al., 1998 | AC |
50.7 | 379. | BG | Katayama, 1988 | Based on data from 334. to 428. K.; AC |
48.3 | 410. | BG | Katayama, 1988 | Based on data from 334. to 428. K.; AC |
49.7 | 388. | A | Stephenson and Malanowski, 1987 | Based on data from 373. to 533. K.; AC |
52.8 | 363. | BG | Baldt and Hall, 1971 | Based on data from 341. to 433. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
384.03 to 472.3 | 1.95374 | 474.908 | -232.81 | Dreisbach and Shrader, 1949 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
14.8 | 260.8 | AC | Blokhin, Paulechka, et al., 2002 | Based on data from 5. to 320. K.; AC |
14.83 | 260.8 | N/A | Maksimuk, Kabo, et al., 1998 | AC |
13.9 | 261. | N/A | Dozen, Fujishima, et al., 1978, 2 | AC |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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
By formula: C12H14N2O2 + H2O = C3H4N2 + CH4O + C8H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -55.48 ± 0.71 | kJ/mol | Cm | Guthrie and Pike, 1987 | liquid phase; Heat of hydrolysis |
By formula: H2O + C8H8O2 = C7H6O2 + CH4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -73.0 ± 1.9 | kJ/mol | Eqk | Guthrie and Cullimore, 1980 | liquid phase |
By formula: C10H14O3 + H2O = 2CH4O + C8H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -17.3 ± 0.4 | kJ/mol | Eqk | Guthrie and Cullimore, 1980 | liquid phase |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References, Notes
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 ± 0.04 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 850.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 819.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.18 | ECD | Kuhn, Levins, et al., 1968 | Done at constant temperature, accuracy uncertain: Chen and Wentworth, 1989;; B |
Gas basicity at 298K
Gas basicity (review) (kJ/mol) | Reference | Comment |
---|---|---|
814.9 ± 0.5 | Decouzon, Gal, et al., 1996 | T = 338K; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.32 ± 0.03 | PI | McLoughlin and Traeger, 1979 | LLK |
9.48 | EI | Elder, Beynon, et al., 1976 | LLK |
9.28 | PE | Behan, Johnstone, et al., 1976 | LLK |
9.4 ± 0.1 | EI | Gilbert, Leach, et al., 1973 | LLK |
9.49 | EI | Benoit, 1973 | LLK |
9.35 ± 0.03 | EI | Johnstone and Mellon, 1972 | LLK |
9.40 ± 0.025 | PE | Johnstone and Mellon, 1972 | LLK |
9.35 ± 0.06 | EI | Foffani, Pignataro, et al., 1964 | RDSH |
9.79 | PE | Cabelli, Cowley, et al., 1982 | Vertical value; LBLHLM |
9.5 | PE | Meeks, Wahlborg, et al., 1981 | Vertical value; LLK |
9.34 | PE | Benoit and Harrison, 1977 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H5+ | 13.9 ± 0.1 | OCH3+CO | EI | Burgers and Holmes, 1982 | LBLHLM |
C6H5+ | 14.3 ± 0.07 | OCH3+CO | EI | Tajima, Azami, et al., 1977 | LLK |
C6H5+ | 14.74 | CH3O+CO | EI | Benoit, 1973 | LLK |
C6H5+ | 13.82 | OCH3+CO | EI | Johnstone and Mellon, 1972 | LLK |
C7H5O+ | 10.5 ± 0.1 | OCH3 | EI | Burgers and Holmes, 1982 | LBLHLM |
C7H5O+ | 10.43 | OCH3 | PI | McLoughlin and Traeger, 1979 | LLK |
C7H5O+ | 10.8 ± 0.05 | OCH3 | EI | Tajima, Azami, et al., 1977 | LLK |
C7H5O+ | 10.83 | OCH3 | EI | Elder, Beynon, et al., 1976 | LLK |
C7H5O+ | 11.40 | OCH3 | EI | Benoit, 1973 | LLK |
C7H5O+ | 10.80 | CH3O | EI | Howe and Williams, 1969 | RDSH |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.