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
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Gas phase thermochemistry data
Go To: Top, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -64.4 ± 1.2 | kcal/mol | Eqk | Guthrie and Cullimore, 1980 | |
ΔfH°gas | -71.66 | kcal/mol | Ccr | Hall and Baldt, 1971 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry 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 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) | 203.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 195.9 | kcal/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) (kcal/mol) | Reference | Comment |
---|---|---|
194.8 ± 0.1 | 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 |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References, Notes
Data compiled by: Coblentz Society, Inc.
- Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)
- SOLUTION (10% IN CCl4 FOR 3800-1350, 10% IN CS2 FOR 1350-450 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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]
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, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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