Benzoic acid, 4-methyl-, methyl ester
- Formula: C9H10O2
- Molecular weight: 150.1745
- IUPAC Standard InChIKey: QSSJZLPUHJDYKF-UHFFFAOYSA-N
- CAS Registry Number: 99-75-2
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: p-Toluic acid, methyl ester; p-Carbomethoxytoluene; Methyl p-methylbenzoate; Methyl p-toluate; Methyl 4-methylbenzoate; Methyl 4-toluate; 4-Methylbenzoic acid, methyl ester; Methyl ester of 4-methylbenzoic acid; p-Toluylic acid, methyl ester; 4-(Methoxycarbonyl)toluene; Methyl p-toluenecarboxylate; NSC 24761; p-(Methoxycarbonyl)toluene
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, 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 |
---|---|---|---|---|---|
ΔfH°solid | -393.3 ± 2.4 | kJ/mol | Cm | Guthrie, Pike, et al., 1992 | Hydrolysis |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔsubH° | 83.3 ± 0.3 | kJ/mol | C | Maksimuk, Kabo, et al., 1998 | AC |
ΔsubH° | 80.6 ± 6.3 | kJ/mol | E | Guthrie, Pike, et al., 1992 | Hydrolysis; ALS |
ΔsubH° | 80.7 | kJ/mol | N/A | Guthrie, Pike, et al., 1992 | DRB |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
376.7 | 0.020 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
51.6 | 418. | Semeniuk and Wilczura-Wachnik, 1998 | Based on data from 403. to 493. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
20.78 | 306.5 | AC | Blokhin, Paulechka, et al., 2002 | Based on data from 5. to 320. K.; AC |
20.77 | 306.5 | AC | Maksimuk, Kabo, et al., 1998 | AC |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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 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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 861.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 830.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.4 | PE | Meeks, Wahlborg, et al., 1981 | LLK |
8.94 ± 0.04 | EI | Foffani, Pignataro, et al., 1964 | RDSH |
9.0 | PE | Meeks, Wahlborg, et al., 1981 | Vertical value; LLK |
De-protonation reactions
C9H9O2- + =
By formula: C9H9O2- + H+ = C9H10O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1515. ± 8.8 | kJ/mol | G+TS | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1487. ± 8.4 | kJ/mol | IMRE | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Mass spectrum (electron ionization)
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: NIST Mass Spectrometry Data Center, William E. Wallace, director
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 | Japan AIST/NIMC Database- Spectrum MS-NW- 688 |
NIST MS number | 229477 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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, Pike, et al., 1992
Guthrie, J.P.; Pike, D.C.; Lee, Y.-C.,
Equilibrium constants and heats of formation of methyl esters and N,N-dimethyl amides of substituted benzoic acids,
Can. J. Chem., 1992, 70, 1671-1683. [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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Semeniuk and Wilczura-Wachnik, 1998
Semeniuk, Bazyli; Wilczura-Wachnik, Hanna,
Vapour--liquid equilibria in the binary and ternary mixtures of methyl benzoate, methyl p-toluate and dimethyl terephthalate,
Fluid Phase Equilibria, 1998, 152, 2, 337-345, https://doi.org/10.1016/S0378-3812(98)00205-2
. [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]
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]
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]
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]
Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D.,
The Nature and Analysis of Substituent Effects,
Prog. Phys. Org. Chem., 1987, 16, 1. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Tboil Boiling point ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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